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SYNLETT

1019 Oligocyclopentadienyl Transition Metal Complexes

C. G. de Azevedo,* K. P. C. Vollhardt*

Accounts and Rapid Communications in Synthetic Organic Chemistry

2002 No. 7 July

1043 Coordination Compounds as Synthetic Building Blocks

Y. Tor*

Br N N Ru (bpy)2 HOOC 2+ Glutathione Na2CO3, H2O/DMF S N N Ru (bpy)2 NH O HN O 2+

COOH H2N

Enantioselective Sulfide Oxidation with H2O2: A Solid Phase and Array Approach for the Optimisation of Chiral Schiff Base-Vanadium Catalysts

B. Pelotier, M. S. Anson,* I. B. Campbell, S. J. F. Macdonald, G. Priem, Rd. F. W. Jackson

1061 Palladium Catalyzed Coupling Reaction of an Enol Nonaflate with (Vinyl)tributylstannanes and Acetylenes

A. Wada,* Yo. Ieki, M. Ito

ONf Pd catalyst R3 R1 R Bu3Sn

1

9

R2 9E- or 9Z-

R2

R3

1065 A Concise Route to the Key Intermediate of (+)Vernolepin Using A Bicyclo[3.2.1]octane Chiral Building Block

N. Miyazawa, K. Ogasawara*

(­) OH known O O H key intermediate H O (+)-vernolepin O OH O

present study O O OMOM

O

Letters

1055

Accounts

IV

Table of Contents

Letters

1069 Manganese(III) Acetate-mediated Alkylation of 1,3-Dicarbonyls to Form Tricarbonyl Compounds Bearing a Quaternary Carbon Centre

G. Bar, A. F. Parsons,* C. B. Thomas

O R1 R3 O R2 Mn(OAc)3, Cu(OAc)2 CH2Cl2, heat OR R4 O R4 O R

1

O R2 R3

81-97%

1073 The Use of Chiral Dithianes for the Synthesis of Chiral a-Oxo-b-Alkyl and Chiral a-Oxo-b-Aryl Esters

E. Tyrrell,* G. A. Skinner, J. Janes, G. Milsom

1077 Novel Preparation of Dihydrooxazines Condensed to Ring D of the Estrane Skeleton

A. Hajnal, J. Wölfling, Gy. Schneider*

1081 Cobalt(I)-catalyzed Neutral Diels­Alder Reactions of Oxygen-functionalized Acyclic 1,3-Dienes with Alkynes

G. Hilt,* K. I. Smolko, B. V. Lotsch

R1 + R2 OR3 CoI R1 R2 OR3 H+ R1 R2 O

1085 A Cyclative Cleavage Approach to the Solid Phase Synthesis of 2-Oxo-1,4-piperazines

J. C. González-Gómez, E. Uriarte-Villares, S. Figueroa-Pérez*

1089 Synthesis of Substituted Cyclopropylphosphonates by Michael Induced Ring Closure (MIRC) Reactions

C. V. Stevens,* G. Van Heecke, C. Barbero, K. Patora, N. De Kimpe, R. Verhé

Table of Contents

V

1093 N-Azinylpyridinium N-Aminides: An Approach to Pyrazolopyridines via an Intramolecular Radical Pathway

A. Nuñez, A. García de Viedma, V. Martínez-Barrasa, C. Burgos, J. Alvarez-Builla*

1097

Intramolecular Diels­Alder Reactions with 6-Hydroxypyranone as Dienophile

F. Richter, C. Maichle-Mössmer, M. E. Maier*

tBuOOH, VO(acac)2 O 3 O toluene, 110 °C O OH 4 48 h (47%) 6 OH CH2Cl2, -30 °C O 1 H H

O 7 OH

8a 4a H

1101 Construction of Terminal Conjugated Enynes: Regioand Stereoselective Syntheses of 3-Alken-1-ynes and 1-Trimethylsilyl-3-alken-1-ynes from Alkenyldialkylboranes and (Trimethylsilyl)ethynyl Bromide

M. Hoshi,* K. Shirakawa

Me3SiC C C H H C Me3SiC C 6 C 3 C R1 H R1 H H C R2B 4 C H R2B C 1 C R H

1

HC C C H H C HC C 5 C 2 C

H R1 H R1

H R1

1105 Convenient Synthesis of 3-(S)-Amino-g-butyrolactone

M. Sibrian-Vazquez, D. A. Spivak*

O O O O HN O O OH 2 steps 93% HCl H2N O

1107 A New Base Mediated Method for the Cleavage of tert-Butyl Esters

S. Paul, R. R. Schmidt*

1109 Efficient Synthesis of ortho-Carborane by Reaction of Propiolic Acid tert-Butyl Ester with Decaborane(14)

L. F. Tietze,* U. Griesbach, O. Elsner

1 52% CO2tBu B10H14, reflux, CH3CN/toluene HC CH B10H10 2 = = BH = CH

Letters

VI

Table of Contents

Letters

1111 An Azido­Hanessian Reaction

M. Baruah, M. Bols*

Ph O O

IN3 MeCN rfx 20 min. 78%

Ph

O O N3

1113 New Chiral Nitrones in the Synthesis of Modified Nucleosides

R. Fischer, A. Drucková, L. Fisera,* A. Rybár, C. Hametner, Micha³. K. Cyrañski

R4O OR3 OR1

7, 12

OR2 N O Bn dipolarophile

toluene, 110°C

OR1 OR3 N

4 5 3 1' 1 2 2' 3' 4'

OR4

O

N Bn

OR2

13a, 14a, 15a

1118 Pd/C as a Highly Active Catalyst for Heck, Suzuki and Sonogashira Reactions

R. G. Heidenreich, K. Köhler,* J. G. E. Krauter, J. Pietsch

R X Heck Suzuki R

R

Sonogashira R

1123 Efficient Palladium-catalyzed Amination and Alkylation of 3-Iodo-6-arylpyridazines

I. Parrot, G. Ritter, C. G. Wermuth, M. Hibert*

R R4 N R5

1

R1 R

R2 R3 Pd I

R1

R2 R3 Pd R3

R1

R2 N R R2 R1 R3

N N

N N Pd R

2

N N N N R3

N N

1128 A Simple Protocol for the One Pot Synthesis of Chiral Secondary Benzylic Alcohols by Catalytic Enantioselective Reduction of Aromatic Ketones

V. L. Ponzo, T. S. Kaufman*

1131 A Convenient Unsymmetric Functionalization of Diaza-21-Crown-7

G. J. Kirkovits, C. D. Hall*

Boc I O O O O I NaH DMF HN O O Boc Boc N O O N Boc O O O O O

TFA

CH2Cl2 NH O O N Boc

+

NH

Table of Contents

VII

1134 CFC- or HFC-Free Approach to a-Substituted b,g,gTrifluoroallyl Alcohols by the Reaction of b-Fluoro-btrifluoromethylated Enol Tosylate with Grignard Reagents

K. Funabiki,* K.-i. Sawa, K. Shibata, M. Matsui*

F3C F 1 H OTs RMgBr THF reflux F2C F 2 OH R H4SiW12O40 EtOH reflux EtO2C F 3 (Z/E = >99/<1) R

1137 Palladium-Catalyzed Coupling Reaction of Alkenylgalliums with Aryl Halides

S. Mikami, H. Yorimitsu, K. Oshima*

Pd cat. GaCl2 + Ar­X Ar

1140 Interaction of Izatins with Some Five-membered Aminoheterocycles

A. O. Pushechnikov,* D. M. Volochnyuk, A. A. Tolmachev

1143 Indium Tribromide Catalyzed Highly Regioselective Ring Opening of Epoxides and Aziridines with Pyrrole

J. S. Yadav,* B. V. S. Reddy, G. Parimala

1146 Ring Closing Metathesis for the Asymmetric Synthesis of (S)-Homopipecolic Acid, (S)-Homoproline and (S)-Coniine

S. G. Davies,* K. Iwamoto, C. A. P. Smethurst, A. D. Smith, H. Rodriguez-Solla

n N Li Ph Conjugate addition N n Ph CO2R n Reduction NH CO2R

Ring Closing CO2R Metathesis

1149 Pd/C-H2-Catalysed Deuterium Exchange Reaction of the Benzylic Site in D2O

H. Sajiki,* K. Hattori, F. Aoki, K. Yasunaga, K. Hirota*

H Ph H R or H Ph R1 R2 10% Pd/C, H2 D2O, rt, 3 days D Ph D R or D Ph R1 R2

(1.0 mmol)

Letters

VIII

Table of Contents

Letters

1152 Synthesis of 2- and 3-Substituted N-Methylpyrroles

E. Dvornikova, K. Kamieñska-Trela*

1155 Porphyrins in 1,3-Dipolar Cycloaddition Reactions: Synthesis of a Novel Pyrazoline-fused Chlorin and a Pyrazole-fused Porphyrin

A. M. G. Silva, A. C. Tomé, M. G. P. M. S. Neves, J. A. S. Cavaleiro*

Ph N HN Ph NO2 N Ph O2N N N H Ph H NH N N CH2 Ph Et2O, rt N HN NH N H Ph

Ph

Ph

1158 An Approach to New, Axially Chiral z-Amino Alcohols Using a Ring Opening Reaction

M. Furegati, A. J. Rippert*

R R O R R R1 N R1

OH

1161 Pd-Catalyzed Carbonylative Cross-coupling Reactions of Chloroarene-Cr(CO)3 Complexes

B. Gotov, J. Kaufmann, H. Schumann, H.-G. Schmalz*

R2 R1 Cl Cr(CO)3 5 atm CO 5 mol% PdCl2(PPh3)2 Me In Me N Me Me R2 R Cr(CO)3 R1 O

or PhB(OH)2 , K2CO3

O

1

2 3

R = Me R = Ph

1164 Generation of a Geminal Dicarbenoid of Chromium: Formation of Allenes from Terminal Alkenes in One-Pot

K. Takai,* R. Kokumai, S. Toshikawa

Cl CCl4 + 4 CrCl2 R THF, 25 °C C CrIII CrIII R Cl

1167 [Rh(OH)(cod)]2 (cod = 1,5-Cyclooctadiene): A Highly Efficient Catalyst for 1,4-Hydrosilylation of a,b-Unsaturated Carbonyl Compounds

A. Mori,* T. Kato

R2 R1 R3 Y = R4 or OR4 O

+

cat. [Rh(OH)(cod)]2 H Si 0.005-0.15 mol % Y R

1

R2

OSi Y R3

Table of Contents

IX

1170 High Throughput Synthesis of Functionalised 1,3-Diones and Subsequent Heterocycle Formation

D. A. Price,* S. Gayton, P. A. Stupple

1173 A New, Highly Selective, Free-Radical Aerobic Oxidation of Silanes to Silanols Catalysed by N-Hydroxyphthalimide under Mild Conditions.

F. Minisci,* F. Recupero, C. Punta, C. Guidarini, F. Fontana, G. F. Pedulli

1,2-Bis-N-[2¢-(diphenylphosphino)-benzo/naphtho]1,2-diamino-cyclo-hexane ­ Trost Modular Ligands

Compiled by I. J. S. Fairlamb

1178

Potassium Monopersulfate Triple Salt [Oxone®]

Compiled by A. V. Narsaiah

Errata

1180

Forthcoming Accounts

XV

The online publication date of Issue 6 was 29.05.2002

Synlett Spotlights

1176

Letters

X

Table of Contents

Author Index

Alvarez-Builla, J. 1093 Anson, M. S. 1055 Aoki, F. 1149 Bar, G. 1069 Barbero, C. 1089 Baruah, M. 1111 Bols, M. 1111 Burgos, C. 1093 Campbell, I. B. 1055 Cavaleiro, J. A. S. 1155 Cyrañski, M. K. 1113 Davies, S. G. 1146 de Azevedo, C. G. 1019 De Kimpe, N. 1089 Drucková, A. 1113 Dvornikova, E. 1152 Elsner, O. 1109 Fairlamb, I. J. S. 1176 Fisera, L. 1113 Figueroa-Pérez, S. 1085 Fischer, R. 1113 Fontana, F. 1173 Funabiki, K. 1134 Furegati, M. 1158 García de Viedma, A. 1093 Gayton, S. 1170 González-Gómez, J. C. 1085 Gotov, B. 1161 Griesbach, U. 1109 Guidarini, C. 1173 Hajnal, A. 1077 Hall, C. D. 1131 Hametner, C. 1113 Hattori, K. 1149 Heidenreich, R. G. 1118 Hibert, M. 1123 Hilt, G. 1081 Hirota, K. 1149 Hoshi, M. 1101 Ieki, Y. 1061 Ito, M. 1061 Iwamoto, K. 1146 Jackson, R. F. W. 1055 Janes, J. 1073 Kamieska-Trela, K. 1152 Kato, T. 1167 Kaufman, T. S. 1128 Kaufmann, J. 1161 Kirkovits, G. J. 1131 Köhler, K. 1118 Kokumai, R. 1164 Krauter, J. G. E. 1118 Lotsch, B. V. 1081 Macdonald, S. J. F. 1055 Maichle-Mössmer, C. 1097 Maier, M. E. 1097 Martínez-Barrasa, V. 1093 Matsui, M. 1134 Mikami, S. 1137 Milsom, G. 1073 Minisci, F. 1173 Miyazawa, N. 1065 Mori, A. 1167 Narsaiah, A. V. 1178 Neves, M. G. P. M. S. 1155 Nuñez, A. 1093 Ogasawara, K. 1065 Oshima, K. 1137 Parimala, G. 1143 Parrot, I. 1123 Parsons, A. F. 1069 Patora, K. 1089 Paul, S. 1107 Pedulli, G. F. 1173 Pelotier, B. 1055 Pietsch, J. 1118 Ponzo, V. L. 1128 Price, D. A. 1170 Priem, G. 1055 Punta, C. 1173 Pushechnikov, A. O. 1140 Recupero, F. 1173 Reddy, B. V. S. 1143 Richter, F. 1097 Rippert, A. J. 1158 Ritter, G. 1123 Rodriguez-Solla, H. 1146 Rybár, A. 1113 Sajiki, H. 1149 Sawa, K.-i. 1134 Schmalz, H.-G. 1161 Schmidt, R. S. 1107 Schneider, Gy. 1077 Schumann, H. 1161 Shibata, K. 1134 Shirakawa, K. 1101 Sibrian-Vazquez, M. 1105 Silva, A. M. G. 1155 Skinner, G. A. 1073 Smethurst, C. A. P. 1146 Smith, A. D. 1146 Smolko, K. I. 1081 Spivak, D. A. 1105 Stevens, C. V. 1089 Stupple, P. A. 1170 Takai, K. 1164 Thomas, C. B. 1069 Tietze, L. F. 1109 Tolmachev, A. A. 1140 Tomé, A. C. 1155 Tor, Y. 1043 Toshikawa, S. 1164 Tyrrell, E. 1073 Uriarte-Villares, L. 1085 Van Heecke, G. 1089 Verhé, R. 1089 Vollhardt, K. P. C. 1019 Volochnyuk, D. M. 1140 Wada, A. 1061 Wermuth, C. G. 1123 Wölfling, J. 1077 Yadav, J. S. 1143 Yasunaga, K. 1149 Yorimitsu, H. 1137

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