Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine Schiff base using a chiral two-center phase-transfer catalyst
Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine Schiff base using a chiral two-center phase-transfer catalyst
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DOI：
10.1002/anie.200500927
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发表时间：
2005-01-01
影响因子：
16.6
通讯作者：
Shibasaki, M
中科院分区：
文献类型：
--
作者：
Okada, A;Shibuguchi, T;Shibasaki, M
以酒石酸衍生二铵盐（TaDiAS）为相转移催化剂，以甘氨酸希夫碱和n保护亚胺为原料，在不对称相转移条件下制备了具有光学活性的α， β-二氨基酸（见方案；Boc=叔丁基羰基）。N原子的化学选择性脱保护使得α， β-二氨基酸产物的直接转化得以进行。
(Chemical Equation Presented) Optically active α, β-diamino acids are prepared under asymmetric phase-transfer reaction conditions from a glycine Schiff base and N-protected imines with a tartrate-derived diammonium salt (TaDiAS) as the phase-transfer catalyst (see scheme; Boc= tert-butoxycarbonyl). Chemoselective deprotection of the N atoms allows straightforward transformations of the α, β-diamino acid products to be carried out.