高度非对映选择性催化的迈尔外因-庞多夫-韦利还原反应
Highly diastereoselective catalytic Meerwein-Ponndorf-Verley reductions.
作者信息
Yin Jingjun, Huffman Mark A, Conrad Karen M, Armstrong Joseph D
机构信息
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA.
出版信息
J Org Chem. 2006 Jan 20;71(2):840-3. doi: 10.1021/jo052121t.
[reaction: see text] Very practical synthesis of ephedrine analogues in high yields and enantiopurity was realized by a highly diastereoselective Meerwein-Ponndorf-Verley (MPV) reduction of protected alpha-amino aromatic ketones using catalytic aluminum isopropoxide. The high anti selectivity resulted from the chelation of the nitrogen anion to the aluminum. In contrast, high syn selectivity was obtained with alpha-alkoxy ketones and other compounds via Felkin-Ahn control.
[反应：见正文] 通过使用异丙醇铝催化对受保护的α-氨基芳基酮进行高度非对映选择性的迈尔外因-彭多夫-韦利（MPV）还原反应，以高收率和对映体纯度实现了麻黄碱类似物的非常实用的合成。高反式选择性源于氮阴离子与铝的螯合作用。相比之下，通过费尔金-安控制，α-烷氧基酮和其他化合物获得了高顺式选择性。
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