A diastereoselective radical cyclisation approach to pyroglutamates

被引：37

作者：

Goodall, K ^{[1
]}

Parsons, AF ^{[1
]}

机构：

[1] UNIV YORK,DEPT CHEM,YORK YO1 5DD,N YORKSHIRE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 03期

关键词：

D O I：

10.1016/S0040-4039(96)02352-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 5-endo radical cyclisation of pyruvic acid derived dehydroalanines which contain chiral ester auxiliaries is reported. Cyclisation of the menthol ester derivative using Bu(3)SnH at 80 degrees C proceeded with low diastereoselectivity (1.75:1) but the selectivity could be increased to 6:1 on cyclisation of the corresponding 8-phenylmethyl ester at 20 degrees C. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：491 / 494

页数：4

共 38 条

[1] DIASTEREOSELECTIVE RADICAL-ADDITION TO METHYLENEOXAZOLIDINONES - AN ENANTIOSELECTIVE ROUTE TO ALPHA-AMINO-ACIDS
AXON, JR
BECKWITH, ALJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (05) : 549 - 550
[2] AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL
BALDWIN, JE
MIRANDA, T
MOLONEY, M
HOKELEK, T
[J]. TETRAHEDRON, 1989, 45 (23) : 7459 - 7468
[3] DIASTEREOSELECTIVE RADICAL-ADDITION TO DERIVATIVES OF DEHYDROALANINE AND OF DEHYDROLACTIC ACID
BECKWITH, ALJ
CHAI, CLL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) : 1087 - 1088
[4] BECKWITH ALJ, 1987, J CHEM SOC P2, V2, P1801
[5] DONOR-ACCEPTOR EFFECTS ON THE STABILITY OF RADICALS DERIVED FROM ALPHA-DIALKYLAMINO KETONES
BORDWELL, FG
GALLAGHER, T
ZHANG, XM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (09) : 3495 - 3497
[6] ORGANIC SYNTHESES VIA FREE-RADICAL DISPLACEMENT REACTIONS OF ORGANOBORANES
BROWN, HC
MIDLAND, MM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (08) : 692 - &
[7] ORGANOBORANES FOR SYNTHESIS .5. STOICHIOMETRICALLY CONTROLLED REACTION OF ORGANOBORANES WITH OXYGEN UNDER MILD CONDITIONS TO ACHIEVE QUANTITATIVE CONVERSION TO ALCOHOLS
BROWN, HC
MIDLAND, MM
KABALKA, GW
[J]. TETRAHEDRON, 1986, 42 (20) : 5523 - 5530
[8] CARDILLO B, 1995, SYNLETT, P1159
[9] METHYLENE PIPERAZINE-2,5-DIONES AS TEMPLATES FOR THE SYNTHESIS OF AMINO-ACID DERIVATIVES
CHAI, CLL
KING, AR
[J]. TETRAHEDRON LETTERS, 1995, 36 (24) : 4295 - 4298
[10] AN ASYMMETRIC-SYNTHESIS OF CROBARBATIC ACID
CHEN, MY
FANG, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) : 2937 - 2941

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