Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 14-15, Pages 2624-2630Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100227
Keywords
asymmetric catalysis; 1,4-dicarbonylbut-2-enes; organocatalysis; alpha-stereogenic amides and ketones; sulfa-Michael addition
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Funding
- NSFC [21072044]
- Excellent Youth Foundation of Henan Scientific Committee [114100510003]
- International Cooperation Foundation of Henan Province [104300510062]
- ARF [R-143-000-337-112]
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Conjugate addition to 1,4-dicarbonylbut-2-enes will generate an alpha-stereogenic center with respect to one of the carbonyl groups, which informally, can be considered as an inversion of normal reactivity patterns or umpolung protocol. In this paper, the addition of tert-butyl mercaptan to 1,4-dicarbonylbut-2-enes including (E)-4-oxo-4-arylbutenamides and (E)-4-oxo-4-arylbutenones has been developed, to synthesize a series of chiral sulfur-substituted a-stereogenic amides and ketones in high regioselectivity and enantioselectivity (up to 98% ee).
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