Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines

被引:29
作者
Agami, C [1 ]
Couty, F [1 ]
Evano, G [1 ]
机构
[1] Univ Paris 06, CNRS, UMR 7611, Lab Synth Asymetr, F-75005 Paris, France
关键词
D O I
10.1016/S0957-4166(00)00462-6
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure beta -amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the beta -amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4639 / 4643
页数:5
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