Facile Construction of Vicinal Quaternary and Tertiary Stereocenters via Regio- and Stereoselective Organocatalytic Michael Addition to Nitrodienes
Facile Construction of Vicinal Quaternary and Tertiary Stereocenters via Regio- and Stereoselective Organocatalytic Michael Addition to Nitrodienes
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DOI：
10.1002/adsc.201100618
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发表时间：
2011-12-01
影响因子：
5.4
通讯作者：
Chimni, Swapandeep Singh
中科院分区：
文献类型：
--
作者：
Chauhan, Pankaj;Chimni, Swapandeep Singh
一个高度区域和立体选择性的协议，合成邻位的四级和三级立体中心已被开发。低催化剂负载量（0.5- 5mol%）的6 '-OH金鸡纳生物碱（BnCPN或BnCPD）在温和的反应条件下以良好至优异的产率（高达> 99）、高对映选择性（高达99%ee）和高非对映选择性（高达> 99：1dr）催化三取代碳亲核试剂与硝基二烯的迈克尔加成。
A highly regio- and stereoselective protocol for the synthesis of vicinal quaternary and tertiary stereocenters has been developed. The 6'-OH Cinchona alkaloids (BnCPN or BnCPD) at low catalyst loading (0.5-5 mol%) catalyze the Michael addition of trisubstituted carbon nucleophiles to nitrodienes in good to excellent yield (up to > 99), high enantioselectivity (up to 99% ee) and high diastereoselectivity (up to > 99:1 dr) under mild reaction conditions.