Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones
Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones
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DOI：
10.1002/chem.201504362
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发表时间：
2015-12-21
影响因子：
4.3
通讯作者：
Cozzi, Pier Giorgio
中科院分区：
文献类型：
--
作者：
Keeri, Abdul Raheem;Gualandi, Andrea;Cozzi, Pier Giorgio
首次将 TosMIC 催化不对称加成到未活化的酮上。 Me2Zn和氨基醇催化剂的组合促进了羟醛加成/环化反应，使恶唑啉具有完全取代的立体中心，具有优异的收率（高达92％）、高对映选择性（高达96％）和完全的非对映选择性。然后，在直接酸水解后，使用手性恶唑啉得到带有叔醇基序的对映体富集的结构单元，例如羟基醛、羟基酸和羟基酯，而无需外消旋化。
The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92%), high enantioselectivities (up to 96 %), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.