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Accounts and Rapid Communications in Synthetic Organic Chemistry

1999 No. 12 December

O

polymerization glycopolymers

J. Kadokawa, H. Tagaya, K. Chiba

polymerizable saccharide monoemrs

1857 The Need for an Incisive Analysis of the Regioselectivity Associated with the Deprotonation of a-Alkoxy and a-Acyloxy Ketones

L. A. Paquette, S. V. O'Neil, N. Guillo, Q. Zeng, D. G. Young

O O

O O + TBSO (1.6 : 1)

O O

TBSOTf, Et3N CH2Cl2, 0 °C

O

TBSO

1867 CuCN-Mediated Intramolecular Conjugate Additions. Syntheses of Functionalized, cis-Fused Bicyclo[6.3.0]undecanes, Bicyclo[6.4.0]dodecanes, and Bicyclo[7.4.0]tridecanes

E. Piers, K. A. Skupinska, D. J. Wallace

O R1 n R2 R1 n R2 m R1 O

O n

R2 O m

SnMe3 m

1871 An Expedient Synthesis of Pyrrole Derivatives by Reaction of Lithiated Methoxyallenes with Imines

M. O. Amombo, A. Hausherr, H.-U. Reissig

1875 Synthesis of a New Chiral Polyamine Template ­ Towards an Active Site Analogue of Vanadium Haloperoxidase

J. A. Martinez-Perez, M. A. Pickel, E. Caroff, W.-D. Woggon

Letters

O

Accounts

1845 Novel Approaches to Glycopolymer Syntheses from the Viewpoint of Polymerization Chemistry

IV

1879 Sequences of Yne-Ene Cross Metathesis and Diels-Alder Cycloaddition Reactions ­ Modular Solid Phase Synthesis of Substituted Octahydrobenzazepinones

S. C. Schürer, S. Blechert

Table of Contents

Letters

O R1 N R3 R2 NH2 R3 O + O R2

R1

O

1883 Regioselective Base-induced Ethereal Bridge Openings of 7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic Derivatives; Synthesis of Squalestatin Core Analogues

N. Jotterand, P. Vogel

E O E OTIPS

TBSO O HO E = COOMe

E E OTIPS

TBSO HO HO

E O E OTIPS

H O TBSO O E

H OTIPS

O OH

1887 Iterative Synthesis of [n]Rotaxanes

A. H. Parham, R. Schmieder, F. Vögtle

1891 Synthesis of Bridged Thiourea Calix-sugar

C. Saitz-Barria, A. Torres-Pinedo, F. Santoyo-González

t-Bu

t-Bu t-Bu

t-Bu

O

OH

OH

O

S

NH

HN

S

Sugar-NH

HN-Sugar

1895 Tandem (Domino) and Two-Directional Asymmetric Catalysis of Carbonyl-Ene Reaction with Fluoral: Fluoral-Ene Approach to Modeling of Inter-Smectic Layer Interaction of Antiferroelectric Liquid Crystals

K. Mikami, T. Yajima, N. Siree, M. Terada, Y. Suzuki, Y. Takanishi, H. Takezoe

OH O Cl2Ti(OiPr)2 MS 4A SR

O CO

OH

OH F3C

O OC

SR

OH CF3

2

F3C H

+

(10 mol%) 0 °C, 2 h

O CF3 CO CF3 O OC

C8H17O

OC8H17

AFLC

1899 BINOL-Ti-Catalyzed Carbonyl-Ene Cyclization by Tuning the 6-Br-Ligand for the Synthesis of 2Methyl-19-nor-22-oxa Vitamin D Analogue with Significant Differentiation Activity1

K. Mikami, Y. Koizumi, A. Osawa, M. Terada, H. Takayama, K. Nakagawa, T. Okano

O

Br OH OH OBn Br 6-Br-BINOL Ti(OPri)

2

O OH OBn

/ Cl2 OMPM

MS 4A

HO

OMPM HO OH

Table of Contents

1903 Synthesis of 2-Amino-2-methyl-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Bislactim Ether Derived from Cyclo[Ala-D-Val] to Vinylphosphonates

M. Ruiz, V. Ojea, M. C. Fernández, S. Conde, A. Díaz, J. M. Quintela

V

1907 Asymmetric Aminohydroxylation of Heteroaromatic Acrylates

D. Raatz, C. Innertsberger, O. Reiser

1911 Novel Molecular Clamp Method for Anomeric Stereocontrol of Glycosylation

M. Wakao, K. Fukase, S. Kusumoto

BnO BnO

X O O O HO O BnO BnO OMe SPh BnO

PhIO, TMSOTf, MS4A

BnO BnO

O X O O O BnO BnO

O BnO OMe

X=

O

tBu

O

tBu

, 86% (: = 99:1) , 77% (: = 3:97)

Si

1915 A Concise Synthesis of (-)-Cytoxazone and its Stereoisomers via Imino 1,2-Wittig Rearrangement

O. Miyata, H. Asai, T. Naito

MeO

NOMe O MeO

NOMe HN OH

O O HO

H H MeO

(-)-cytoxazone

1917 Novel Intramolecular Cyclisations Involving Ketene Radical Intermediates as an Approach to the Synthesis of Polyquinanes

N. M. Harrington-Frost, G. Pattenden

O COSePh Bu3SnH AIBN H

1919 A Concise, Asymmetric Synthesis of Methyl (1S,2R)1-Amino-2,3-dihydro-1H-indene-2-carboxylate: A Novel, Constrained b-Amino Ester

D. A. Price

Letters

VI

1921 Anti-Markovnikov Addition of Thiols Across Double Bonds Catalyzed by H-Rho-Zeolite

P. Kumar, R. K. Pandey, V. R. Hegde

Table of Contents

Letters

1923 A Convenient Method for the N-Acylation and Esterification of Hindered Amino Acids: Synthesis of Ultra Short Acting Opioid Agonist, Remifentanil

M. J. Coleman, M. D. Goodyear, D. W. S. Latham, A. J. Whitehead

1925 Cycloaddition Reactions of Iodonium Ylides of Cyclic b-Diketones with 1,3-Dienes: Evidence for a Stepwise Mechanism.

I. Alexiou, E. P. Gogonas, L. P. Hadjiarapoglou

1927 Distannoxane-Catalyzed Selective Acetylation of 3-Chloropropane-1,2-diol: A Convenient Synthesis of Enantiopure Epichlorohydrin

A. Orita, T. Ito, Y. Yasui, J. Otera

Cl OH

OH

Cl OH

OAc

Cl Br

OAc

Cl Br

OH

Cl

O

1930 Tetrakis(dimethylamino)ethylene (TDAE) as a Potent Electron Source for Cr-Mediated Allylation of Aldehydes and Ketones

M. Kuroboshi, K. Goto, M. Mochizuki, H. Tanaka

R1

O R 1 Br 2+ 2

TDAE (200 mol%) NiBr2 (5 mol%) CrCl3 (30 mol%)

OH

1 Me3SiCl (150 mol%) R R2 DMF, room temp

3 TDAE: (Me2N)2C C(NMe2)2

1933 A Novel Approach to the Solid-Phase Synthesis of (Acyloxy)methyl Ketones

M. T. Mujica, G. Jung

Table of Contents

1936 Asymmetric Synthesis of Cyclopropane-1,1-Dicarboxylates from a g-Alkoxy-Alkylidenemalonate

A. Krief, L. Provins, A. Froidbise

VII

1939 First Synthesis of Metallated Titanacyclopropenes

C. Averbuj, J. Kaftanov, I. Marek

R X + Ti(OiPr)4

Et2O iPrMgBr - 78°C to -50°C

R Ti iPrO

TiX(OiPr)2

OiPr

1942 Cu(I)-Catalyzed Regioselective Synthesis of Substituted Allyl Furans and Thiophenes Using Organostannanes

N. S. Nudelman, C. Carro

1945 Synthesis of a trans-Fused Tricyclic Ether Using a Novel Differentially Protected Glucal

M. A. Leeuwenburgh, C. Kulker, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom

1948 Efficient Syntheses of Cyclopropylacetylene, a Crucial Synthetic Intermediate for Efavirenz (DMP-266)

S. E. Schmidt, R. N. Salvatore, K. W. Jung, T. Kwon

Cl

F3C O N O H Efavirenz (DMP-266)

1951 DBU-MeOH Promoted One-Pot Stereoselective g-Functionalization of 1,3-Dicarbonyls: Reactivity of b-Ketoamides Towards a,b-Unsaturated Aldehydes

E. Charonnet, M.-H. Filippini, J. Rodriguez

Letters

VIII

1954 1,3,4,5-Tetrahydroazepin-2-ones by Dearomatising Anionic Cyclisation of N-Allyl-1-Naphthamides

A. Ahmed, J. Clayden, M. Rowley

O N 1. t-BuLi 2. DMPU 3. E+

Table of Contents

Letters

O E

N

H 48-73%

1957 Two Efficient N-Acylation Methods Mediated by Solid-Supported Reagents for Weakly Nucleophilic Heterocyclic Amines

K. Kim, K. Le

R1NH2

i)

O

NO2 O O R2

O R1 N H O R1 N H R3 R2

ii) Amberlite IRA-120 i) BEMP, R3COCl ii) Trisamine

1960 Deprotection of Acetals and Silyl Ethers Using a Polymer-Supported p-Acid Catalyst: Chemoselectivity and Polymer Effect

N. Tanaka, Y. Masaki

O

O O P

P

= MOM, TBDPS

O O

O O P

NC NC (CH2)n OTBDMS O P

O O

O

O

polymer cat. CH3CN / H2O (9 : 1), 0 °C ~ r.t. (CH2)n P = THP, MOM, TBDPS OH O P

1963 Ytterbium Triflate Mediated Selective Deprotection of Acetates

G. V. M. Sharma, A. Ilangovan

1666 The Triumph of Zinc: A Short and Highly Efficient Synthesis of the Calyculin C1-C9 Tetraene Building Block by Negishi Coupling

P. M. Pihko, A. M. P. Koskinen

Br Bu3Sn ZnCl

CO2Me Bu3Sn CO2Me

Pd(PPh3)4 95% only coupling product

1969 Asymmetric Synthesis of Tetrasubstituted Tetrahydrofuran, 2-Epigoniothalesdiol, Employing Stereoselective Hydrogenation

H. Yoda, T. Shimojo, K. Takabe

OH HOOC OH COOH

SBTO

OTBS

O

N

O HO OH

CH2Ph

2

O

5

COOCH3

Table of Contents

1972 A Concise Synthesis of N-(Trideuteromethyl)morpholine-N-oxide Monohydrate

T. Rosenau, A. Potthast, P. Kosma

IX

1975 Synthesis of 1,1'-Bis(phosphetano)ferrocenes, a New Class of Chiral Ligands for Asymmetric Catalysis

A. Marinetti, F. Labrue, J.-P. Genêt

1978 Generation and Capture of Iminyl Radicals from Ketoxime Xanthates

F. Gagosz, S. Z. Zard

1981 Kinetic Enzymatic Resolution of Cyclopropane Derivatives

J. Pietruszka, T. Wilhelm, A. Witt

1984 Practical and Efficient Chlorination of Deactivated Anilines and Anilides with NCS in 2-Propanol

A. Zanka, A. Kubota

NH2 NCS 2-PrOH CN

NH2 Cl

CN 96 %

1987 Asymmetric Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagent to N-Borylimines

S. Itsuno, A. Yokoi, S. Kuroda

R CN

LiEt3BH R

N

BEt3Li Chirally modified allylboron reagent H

NH2 R *

Letters

X

1990 Scandium and Ytterbium Tris(perfluorobutanesulfonyl)methide Complexes: Extremely Efficient Lewis Acid Catalysts

J. Nishikido, F. Yamamoto, H. Nakajima, Y. Mikami, Y. Matsumoto, K. Mikami

Table of Contents

Letters

O O O C C4F9 S C Ln C 3 O Ln=Sc, Yb O S C4F9 O O S C4F9

3 3

Cat. (5 mol%) benzotrifluoride 50 °C, 3 h OMe Sc[C(SO2C4F9)3]3 Yb[C(SO2C4F9)3]3 cf. Sc(OTf)3 Yb(OTf)3 OMe 93% (89%, 1h) 91% 48% 12%

1993 A New Quinazoline Synthesis

H. Kotsuki, H. Sakai, H. Morimoto, H. Suenaga

X

F

HN

R

+

CHO

K2CO3, MS 4A X

N N X = CN, NO2 R = Ar, alkyl

R

NH2·HCl CH3CN,

1996 Copper (I) Oxide Mediated Perfluoroalkylation of Anilines

M. Moreno-Mañas, R. Pleixats, S. Villarroya

NH2 IC8F17, Cu2O DMSO, 130 °C

NH2 C8F17 C8F17

C8F17

1999 Facile Preparation of (Phosphorylalkyl)-Functionalized Cyclopropanols and Cyclopropylamines

H. Winsel, V. Gazizova, O. Kulinkovich, V. Pavlov, A. de Meijere

2004 Tricarbonyl(dihydroazepinyl)chromium Complexes and Methylenepyrrolidines from (2'-Dimethylaminoethenyl)carbenechromium Complexes

H. Schirmer, T. Labahn, B. Flynn, Y.-T. Wu, A. de Meijere

New Tools in Synthesis

1679 Organic Synthesis Supported by Antibody Catalysis

J. Hasserodt

Table of Contents

2023 Scandium Triflate

Compiled by D. Longbottom

XI

Indexes 1999 Errata

2024 2040

Synlett Spotlight

XII

Table of Contents

Author Index

Ahmed, A. 1954 Alexiou, I. 1925 Amombo, M. O. 1871 Asai, H. 1915 Averbuj, C. 1939 Blechert, S. 1879 Caroff, E. 1875 Carro, C. 1942 Charonnet, E. 1951 Chiba, K. 1845 Clayden, J. 1954 Coleman, M. J. 1923 Conde, S. 1903 Díaz, A. 1903 de Meijere, A. 1999, 2004 Fernández, M. C. 1903 Filippini, M.-H. 1951 Flynn, B. 2004 Froidbise, A. 1936 Fukase, K. 1911 Gagosz, F. 1978 Gazizova, V. 1999 Geen, G. 2024 Genêt, J.-P. 1975 Gogonas, E. P. 1925 Goodyear, M. D. 1923 Goto, K. 1930 Guillo, N. 1857 Hadjiarapoglou, L. P. 1925 Harrington-Frost, N. M. 1917 Hasserodt, J. 2007 Hausherr, A. 1871 Hegde, V. R. 1921 Ilangovan, A. 1963 Innertsberger, C. 1907 Ito, T. 1927 Itsuno, S. 1987 Jotterand, N. 1883 Jung, G. 1933 Jung, K. W. 1948 Kadokawa, J. 1845 Kaftanov, J. 1939 Kim, K. 1957 Koizumi, Y. 1899 Koskinen, A. M. P. 1966 Kosma, P. 1972 Kotsuki, H. 1993 Krief, A. 1936 Kubota, A. 1984 Kulinkovich, O. 1999 Kulker, C. 1945 Kumar, P. 1921 Kuroboshi, M. 1930 Kuroda, S. 1987 Kusumoto, S. 1911 Kwon, T. 1948 Labahn, T. 2004 Labrue, F. 1975 Latham, D. W. S. 1923 Le, K. 1957 Leeuwenburgh, M. A. 1945 Longbottom, D. 2023 Marek, I. 1939 Marinetti, A. 1975 Martinez-Perez, J. A. 1875 Masaki, Y. 1960 Matsumoto, Y. 1990 Mikami, K. 1895, 1899, 1990 Mikami, Y. 1990 Miyata, O. 1915 Mochizuki, M. 1930 Moreno-Mañas, M. 1996 Morimoto, H. 1993 Mujica, M. T. 1933 Naito, T. 1915 Nakagawa, K. 1899 Nakajima, H. 1990 Nishikido, J. 1990 Nudelman, N. S. 1942 O'Neil, S. V. 1857 Ojea, V. 1903 Okano, T. 1899 Orita, A. 1927 Osawa, A. 1899 Otera, J. 1927 Overkleeft, H. S. 1945 Pandey, R. K. 1921 Paquette, L. A. 1857 Parham, A. H. 1887 Pattenden, G. 1917 Pavlov, V. 1999 Pickel, M. A. 1875 Piers, E. 1867 Pietruszka, J. 1981 Pihko, P. M. 1966 Pleixats, R. 1996 Potthast, A. 1972 Price, D. A. 1919 Provins, L. 1936 Quintela, J. M. 1903 Raatz, D. 1907 Reiser, O. 1907 Reissig, H.-U. 1871 Rodriguez, J. 1951 Rosenau, T. 1972 Rowley, M. 1954 Ruiz, M. 1903 Saitz-Barria, C. 1891 Sakai, H. 1993 Salvatore, R. N. 1948 Santoyo-González, F. 1891 Schirmer, H. 2004 Schmidt, S. E. 1948 Schmieder, R. 1887 Schürer, S. C. 1879 Sharma, G. V. M. 1963 Shaw, C. J. 2024 Shimojo, T. 1969 Siree, N. 1895 Skupinska, A. 1867 Suenaga, H. 1993 Suzuki, Y. 1895 Sweeney, J. B. 2024 Tagaya, H. 1845 Takabe, K. 1969 Takanishi, Y. 1895 Takayama, H. 1899 Takezoe, H. 1895 Tanaka, H. 1930 Tanaka, N. 1960 Terada, M. 1895, 1899 Torres-Pinedo, A. 1891 van Boom, J. H. 1945 van der Marel, G. A. 1945 Villarroya, S. 1996 Vogel, P. 1883 Vögtle, F. 1887 Wakao, M. 1911 Wallace, D. J. 1867 Whitehead, A. J. 1923 Wilhelm, T. 1981 Winsel, H. 1999 Witt, A. 1981 Woggon, W.-D. 1875 Wu, Y.-T. 2004 Yajima, T. 1895 Yamamoto, F. 1990 Yasui, Y. 1927 Yoda, H. 1969 Yokoi, A. 1987 Young, D. G. 1857 Zanka, A. 1984 Zard, S. Z. 1978 Zeng, Q. 1857

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