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4‐Aminothiourea Prolinol tert ‐Butyldiphenylsilyl Ether: A Chiral Secondary Amine‐Thiourea as Organocatalyst for Enantioselective anti ‐Mannich Reactions
Author(s) -
Zhang Hui,
Chuan Yongming,
Li Zhengyu,
Peng Yungui
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900399
Subject(s) - chemistry , thiourea , enantioselective synthesis , amine gas treating , organocatalysis , mannich reaction , organic chemistry , catalysis , ether , combinatorial chemistry
anti ‐Selective Mannich reactions of N ‐ p ‐methoxyphenyl (PMP)‐protected α‐iminoglyoxylate with unmodified aldehydes or ketones were effectively catalyzed by 4‐aminothiourea prolinol tert ‐butyldiphenylsilyl ether. The reactions led to chiral β‐amino carbonyl compounds in high yields (up to 94%), excellent diastereo‐ and enantioselectivities (up to 98% de and >99% ee ). The study demonstrated for the first time that direct Mannich‐type reactions of unmodified aldehydes or ketones to α‐iminoglyoxylate can be promoted by secondary amine‐thiourea chiral organocatalyst.