Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction
Advantage of in situ generation of N-arylsulfonyl imines from α-amide sulfones in the phase-transfer-catalyzed asymmetric Strecker reaction
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DOI：
10.1016/j.tetlet.2006.12.122
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发表时间：
2007-02-19
影响因子：
1.8
通讯作者：
Maruoka, Keiji
中科院分区：
文献类型：
--
作者：
Ooi, Takashi;Uematsu, Yukitaka;Maruoka, Keiji
以手性碘化季铵（R，R，R）-1为相转移催化剂，在甲苯-氰化钾水溶液两相条件下，实现了由相应的α-氨基砜高效催化对映选择性合成N-芳基磺酰基α-氨基腈。涉及原位产生反应性N-磺酰亚胺的Strecker合成有利于具有伯和仲烷基取代基的底物的氰化。(c)2006爱思唯尔有限公司保留所有权利。
Highly efficient, catalytic enantioselective synthesis of N-arylsulfonyl alpha-amino nitriles from the corresponding alpha-amido sulfones has been achieved under toluene-aqueous potassium cyanide biphasic conditions using chiral quaternary ammonium iodide (R,R,R)-1 as an effective phase-transfer catalyst. This Strecker synthesis involving the in situ generation of the reactive N-sulfonyl imines is advantageous for the cyanation of the substrates having primary and secondary alkyl substituents. (c) 2006 Elsevier Ltd. All rights reserved.