Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 17, Pages 2690-2694Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800248
Keywords
aldols; ketones; organocatalysis; quaternary; stereocenters; water
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Funding
- National Natural Science Foundation of China [20172064, 203900502, 20532040]
- Shanghai Natural Science Council
- Foundation of National Natural Science Foundation of China [20525208]
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The asymmetric construction of quaternary carbon centers via cross-aldol reactions of ketones with beta,gamma-unsaturated keto esters catalyzed by 4-(tert-butyldiphenylsilyloxy)-pyrrolidine-2-carbox-ylic acid in water is described. The adducts bearing two adjacent chiral centers were obtained in high yields, mostly up to 99% ee, and with high diastereoselectivities. The corresponding polyfunctional products could also be easily transformed to useful lactones with three chiral centers.
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