Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 14-15, Pages 2288-2294Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900399
Keywords
beta-amino carbonyl compounds; 4-aminothiourea prolinol tert-butyldiphenylsilyl ether; asymmetric anti-Mannich reactions; secondary amine-thiourea organocatalyst
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Funding
- Natural Science Foundation of China (NSFC) [20872120, 20572087]
- Program for New Century Excellent Talents [NCET-06-0772]
- Ministry of Education, P R. China [106141]
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anti-Selective Mannich reactions of N-p-methoxyphenyl (PMP)-protected alpha-iminoglyoxylate with unmodified aldehydes or ketones were effectively catalyzed by 4-aminothiourea prolinol tert-butyldiphenylsilyl ether. The reactions led to chiral beta-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 alpha-iminoglyoxylate can be promoted by secondary amine-thiourea chiral organocatalyst.
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