Enantioselective synthesis of 4-unsubstituted 3-alkoxy- and 3-aminoazetidin-2-ones from formaldehyde N,N-dialkylhydrazones

被引：0
作者：
Fernández, R
Ferrete, A
Lassaletta, JM
Llera, JM
Monge, A
机构：
[1] Univ Sevilla, CSIC, Inst Invest Quim, Seville 41092, Spain
[2] Univ Sevilla, Dept Quim Organ & Farmaceut, Seville 41081, Spain
[3] Univ Sevilla, Dept Quim Organ, Seville, Spain
[4] CSIC, Inst Ciencia Mat Madrid, Madrid, Spain
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2000年 / 39卷 / 16期
关键词：
asymmetric synthesis; cycloadditions; hydrazones; ketenes; lactams;
D O I：
10.1002/1521-3773(20000818)39:16<2893::AID-ANIE2893>3.0.CO;2-E
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Playing two roles at once, chiral amines from L-proline or D-mannitol act as protecting groups and as chiral auxiliaries in the [2+2] cyclo-addition of formaldehyde hydrazones, such as 1, to ketenes. This strategy, based on the stability of the hydrazones as methanimines and on the development of a new oxidative cleavage of hydrazides, provides a short entry to enantiopure 4-unsubstituted 3-alkoxy- and 3-aminoazetidinones with desired configurations. X=OBn, N(CO<SUB2>Bn)Bn; Bn=benzyl; MMPP=magnesium monoperoxyphthalate.
引用
收藏
页码：2893 / 2897
页数：5
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