Efficient tin hydride-mediated radical cyclisation of secondary amides leading to substituted pyrrolidinones. Part 2. Application to the synthesis of aromatic kainic acid analogues

被引：26

作者：

Bryans, JS

Large, JM

Parsons, AF ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

[2] Univ Cambridge, Parke Davis Neurosci Res Ctr, Cambridge CB2 2QB, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 20期

关键词：

D O I：

10.1039/a905809e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of phenyl allokainoid, starting from D-serine, is reported. Tin-mediated cyclisation of a secondary amide was used in the key step to produce a trisubstituted pyrrolidinone in excellent yield (ca. 80%). The predominant formation of the all-trans diastereoisomer is consistent with a reversible cyclisation to give the thermodynamically more stable product.

引用

页码：2905 / 2910

页数：6

共 12 条

[1] Towards a versatile synthesis of kainoids .2. Two methods for establishment of C-4 stereochemistry
Baldwin, JE
Bamford, SJ
Fryer, AM
Rudolph, MPW
Wood, ME
[J]. TETRAHEDRON, 1997, 53 (14) : 5255 - 5272
[2] Towards a versatile synthesis of kainoids .3. Efficient methods for control of C-4 stereochemistry
Baldwin, JE
Fryer, AM
Spyvee, MR
Whitehead, RC
Wood, ME
[J]. TETRAHEDRON, 1997, 53 (14) : 5273 - 5290
[3] THE KINETICS AND MECHANISM OF RING-OPENING OF RADICALS CONTAINING THE CYCLOBUTYLCARBINYL SYSTEM
BECKWITH, ALJ
MOAD, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (07): : 1083 - 1092
[4] EFFECT OF NON-BONDED INTERACTIONS ON THE REGIOSELECTIVITY OF CYCLIZATION OF THE HEX-5-ENYL RADICAL
BECKWITH, ALJ
LAWRENCE, T
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (11): : 1535 - 1539
[5] RADICAL TRANSLOCATION REACTIONS OF VINYL RADICALS - SUBSTITUENT EFFECTS ON 1,5-HYDROGEN-TRANSFER REACTIONS
CURRAN, DP
SHEN, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6051 - 6059
[6] SYNTHESIS OF ENANTIOMERICALLY PURE 4-SUBSTITUTED GLUTAMIC ACIDS AND PROLINES - GENERAL ALDOL REACTION OF PYROGLUTAMATE LACTAM LITHIUM ENOLATE MEDIATED BY ET(2)O-CENTER-DOT-BF3
EZQUERRA, J
PEDREGAL, C
YRURETAGOYENA, B
RUBIO, A
CARRENO, MC
ESCRIBANO, A
RUANO, JLG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) : 2925 - 2930
[7] STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS
EZQUERRA, J
PEDREGAL, C
RUBIO, A
YRURETAGOYENA, B
ESCRIBANO, A
SANCHEZFERRANDO, F
[J]. TETRAHEDRON, 1993, 49 (38) : 8665 - 8678
[8] TOTAL SYNTHESIS OF BALANOL AND DESIGNED ANALOGS
NICOLAOU, KC
KOIDE, K
BUNNAGE, ME
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 1995, 1 (07) : 454 - 466
[9] Recent developments in kainoid amino acid chemistry
Parsons, AF
[J]. TETRAHEDRON, 1996, 52 (12) : 4149 - 4174
[10] A HIGHLY EFFICIENT FREE-RADICAL APPROACH TO TRISUBSTITUTED PYRROLIDINONES
PARSONS, AF
TAYLOR, JK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) : 1224 - 1225

← 1 2 →