Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct Mannich reaction under phase-transfer conditions
Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct Mannich reaction under phase-transfer conditions
复制标题
DOI：
10.1021/ol049215u
复制
发表时间：
2004-07-08
期刊：
影响因子：
5.2
通讯作者：
Maruoka, K
中科院分区：
文献类型：
--
作者：
Ooi, T;Kameda, M;Maruoka, K
以N-螺环C-2对称的手性季铵盐2为催化剂，实现了甘氨酸席夫碱3与α-亚胺酯4的相转移催化直接Mannich反应，反应具有较高的对映选择性。这种方法能够催化不对称合成差异保护的3-氨基天冬氨酸，酒石酸二烷基的含氮类似物。产物(syn-5)转化为链甲酸内酰胺前体(6)。
Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.