Ester-enolate Claisen rearrangement of proline-containing α-acyloxy-α-vinylsilane.: Synthesis of pyrrolidine-fused glutamate analogs

被引：16

作者：

Sakaguchi, Kazuhiko ^{[1
]}

Yamamoto, Masahiro ^{[1
]}

Watanabe, Yusuke ^{[1
]}

Ohfune, Yasufumi ^{[1
]}

机构：

[1] Osaka City Univ, Dept Mat Sci, Grad Sch Med, Osaka 5588585, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 28期

关键词：

ester-enolate Claisen rearrangement; alpha-hydroxysilane; alpha-acyloxysilane; Z-enolate; proline; alpha-substituted-proline; chirality transfer;

D O I：

10.1016/j.tetlet.2007.05.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective syntheses of pyrrolidine-fused aspartate and glutamate analogs, (S)-alpha-carboxymethyl-proline 3 and (S)-alpha-2-carboxyethyl-proline 4, using a chirality-transferring ester-enolate Claisen rearrangement of alpha-vinyl-alpha-acyloxysilane having a Boc-Pro as an acyloxy group, are described. The stereochemical outcome of the proline ester-derived ester-enolate Claisen rearrangement is also disclosed. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：4821 / 4824

页数：4

共 28 条

[1]

ALTENBACH HJ, 1991, ORGANIC SYNTHESIS HI, P116

[2]

[Anonymous], ALDRICHIMICA ACTA

[3] New aspects of the Ireland and related Claisen rearrangements [J].

Chai, YH ;

Hong, SP ;

Lindsay, HA ;

McFarland, C ;

McIntosh, MC .

TETRAHEDRON, 2002, 58 (15) :2905-2928

[4]

Dingledine R, 1999, PHARMACOL REV, V51, P7

[5] SYNTHETIC APPROACHES TO BREVIANAMIDE-A AND BREVIANAMIDE-B .1. PREPARATION OF 4-PARA-METHOXYBENZYL-5-(1'-CARBOMETHOXY-2'-[1'',1''-DIMETHYLALLYL-2',3'DIHYDROINDOLE]METHYLIDENE)-1,2-L-PYROLIDINOPIPERAZINE-3,6-DIONE VIA AN IRELAND ESTER ENOLATE CLAISEN REARRANGEMENT [J].

DUNKERTON, LV ;

CHEN, H ;

MCKILLICAN, BP .

TETRAHEDRON LETTERS, 1988, 29 (21) :2539-2542

[6] Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis [J].

Enders, D ;

Knopp, M ;

Schiffers, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (07) :1847-1882

[7] STEREOCHEMICAL CONTROL IN THE ESTER ENOLATE CLAISEN REARRANGEMENT .1. STEREOSELECTIVITY IN SILYL KETENE ACETAL FORMATION [J].

IRELAND, RE ;

WIPF, P ;

ARMSTRONG, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :650-657

[8] ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION [J].

IRELAND, RE ;

MUELLER, RH ;

WILLARD, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2868-2877

[9] Total synthesis of (-)-kaitocephalin [J].

Kawasaki, M ;

Shinada, T ;

Hamada, M ;

Ohfune, Y .

ORGANIC LETTERS, 2005, 7 (19) :4165-4167

[10] SYNTHESIS OF UNSATURATED AMINO-ACIDS BY [3,3]-SIGMATROPIC REARRANGEMENT OF CHELATE-BRIDGED GLYCINE ESTER ENOLATES [J].

KAZMAIER, U .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (09) :998-999

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