Asymmetric synthesis of α-amino-1,3-dithianes via chiral N-phosphonyl imine-based Umpolung reaction without using chromatography and recrystallization.
Asymmetric synthesis of α-amino-1,3-dithianes via chiral N-phosphonyl imine-based Umpolung reaction without using chromatography and recrystallization.
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DOI：
10.1021/jo200070d
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发表时间：
2011-04-15
影响因子：
3.6
通讯作者：
Li, Guigen
中科院分区：
文献类型：
--
作者：
Kattamuri, Padmanabha V.;Ai, Teng;Pindi, Suresh;Sun, Yinwei;Gu, Peng;Shi, Min;Li, Guigen
通过2-锂-1，3-二噻烷与手性N-膦酰亚胺的不对称Umpolung反应，合成了一系列α-氨基-1，3-二噻烷类化合物，产率高达82%，非对映选择性>99：1。发现将手性N-膦酰亚胺缓慢加入到2-锂-1，3-二噻烷溶液中的加成方式对获得优异的非对映选择性至关重要。目前的合成被证明遵循差距化学（基团-辅助-纯化化学）方法，其避免了色谱或重结晶的传统纯化技术，即，用己烷或己烷-乙酸乙酯的混合物洗涤固体粗产物，容易地获得连接有手性N-膦酰基的纯手性α-氨基-1，3-二噻烷。
A series of α-amino-1,3-dithianes have been synthesized via the asymmetric Umpolung reaction of 2-lithio-1,3-dithianes with chiral N-phosphonyl imines in good chemical yields (up to 82%) and good to excellent diastereoselectivities (>99:1). The addition manner by which chiral N-phosphonyl imines are slowly added into the solution of 2-lithio-1,3-dithiane was found to be crucial for achieving excellent diastereoselectivity. The current synthesis was proven to follow the GAP chemistry (Group-Assistant-Purification chemistry) process which avoids traditional purification techniques of chromatography or recrystallization, i.e., the pure chiral α-amino-1,3-dithianes attached with the chiral N-phosphonyl group were readily obtained by washing the solid crude products with hexane or the mixture of hexane-ethyl acetate.
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3
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通讯作者：
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影响因子：
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