A convenient access to (3S)-3-(triisopropylsilyl)oxy-1-pyrroline N-oxide, a useful intermediate for polyfunctionalized enantiopure indolizidine and pyrrolizidine synthesis

被引：53

作者：

Goti, A ^{[1
]}

Cacciarini, M ^{[1
]}

Cardona, F ^{[1
]}

Brandi, A ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, CNR, CSCEA, I-50121 Florence, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

关键词：

nitrones; indolizidines; pyrrolizidines; asymmetric synthesis;

D O I：

10.1016/S0040-4039(99)00310-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optimization of a strategy providing the enantiomerically pure nitrone 2 in five steps and 28% overall yield from L-malic acid has been achieved by the combined use of DIBAL-H as the reductant and triisopropylsilyl as the protecting group. The utility of nitrone 2 as synthetic intermediate is demonstrated by a ready access to polyhydroxylated indolizidines and pyrrolizidines via stereoselective 1,3-dipolar cycloaddition reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2853 / 2856

页数：4

共 3 条

[1] Synthesis of (R)- and (S)-3-(tert-butyldimethylsilyloxy)-1-pyrroline N-oxides -: chiral nitrones for synthesis of biologically active pyrrolidine derivative, Geissman-Waiss lactone
Murahashi, S
Ohtake, H
Imada, Y
TETRAHEDRON LETTERS, 1998, 39 (18) : 2765 - 2766
[2] Solid-phase access to polyhydroxypyrrolizidines by 1,3-dipolar cycloaddition of (S)-3-alkoxypyrroline N-oxide to maleate and crotonate derivatives
Pisaneschi, F
Della Monica, C
Cordero, FM
Brandi, A
TETRAHEDRON LETTERS, 2002, 43 (33) : 5711 - 5714
[3] Asymmetric synthesis of N-protected 3-methylpiperidin-2-one and its diastereoisomer(3S)-1-[(R)-2-羟基-1-苯乙基]-3-甲基-2-哌啶酮的合成
Xiao-zhong Wang
Xia Wang
Ying-qi Chen
Li-yan Dai
Xing-cong Li
Journal of Zhejiang University-SCIENCE A, 2016, 17 : 163 - 170

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