New strategy for the synthesis of 3-substituted prolines

被引：68

作者：

Karoyan, P ^{[1
]}

Chassaing, G ^{[1
]}

机构：

[1] UNIV PARIS 06,CNRS,LAB CHIM ORGAN BIOL,F-75252 PARIS 05,FRANCE

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(96)02221-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring formation involving a Sere trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an alpha-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：85 / 88

页数：4

共 9 条

[1] CONFORMATIONALLY CONSTRAINED AMINO-ACIDS - SYNTHESIS AND OPTICAL RESOLUTION OF 3-SUBSTITUTED PROLINE DERIVATIVES
CHUNG, JYL
WASICAK, JT
ARNOLD, WA
MAY, CS
NADZAN, AM
HOLLADAY, MW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 270 - 275
[2] FREE-RADICAL CYCLIZATIONS
JULIA, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (11) : 386 - &
[3] C-DERIVATIZATION OF AMINO ACIDS . SYNTHESIS AND ABSOLUTE CONFIGURATION OF 3-METHYLPROLINE . CIS-TRANS ISOMERS WITH UNUSUAL VICINAL PROTON COUPLING
KOLLONITSCH, J
SCOTT, AN
DOLDOURAS, GA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (15) : 3624 - +
[4] Stereoselective synthesis of L-[1-C-13], L-[2-C-13] and L-[N-15] amino acids
Martin, A
Chassaing, G
Vanhove, A
[J]. ISOTOPES IN ENVIRONMENTAL AND HEALTH STUDIES, 1996, 32 (01) : 15 - 19
[5] METHCOHN O, 1986, J CHEM SOC CHEM COMM, V9, P695
[6] INTRAMOLECULAR CARBOMETALATION OF SECONDARY ORGANOZINC REAGENTS
MEYER, C
MAREK, I
COURTEMANCHE, G
NORMANT, JF
[J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6053 - 6056
[7] INTRAMOLECULAR METALLO-ENE-ALLENE REACTIONS - A NEW CARBOCYCLES SYNTHESIS
MEYER, C
MAREK, I
COURTEMANCHE, G
NORMANT, JF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) : 863 - 871
[8] RATHKE MW, 1971, TETRAHEDRON LETT, V43, P3995
[9] CYCLIZATION OF METHYL 6,7-EPOXYCITRONELLATE TO METHYLCYCLOPENTANE DERIVATIVES - ALKOXIDE INDUCED CONVERSION OF GAMMA-LACTONES TO GAMMA,DELTA-UNSATURATED ACIDS
WOLINSKY, J
HULL, P
WHITE, EM
[J]. TETRAHEDRON, 1976, 32 (12) : 1335 - 1338

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