Highly Selective Rhodium-Catalyzed Conjugate Addition Reactions of 4-Oxobutenamides

A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to >99:1, >96% ee) and moderate to excellent yields (54−99%). The key to high selectivity is the use of sterically demanding P-chiral...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-11, Vol.72 (23), p.8870-8876
Main Authors: Zigterman, Jamie L, Woo, Jacqueline C. S, Walker, Shawn D, Tedrow, Jason S, Borths, Christopher J, Bunel, Emilio E, Faul, Margaret M
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Organic chemistry
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Summary:A variety of 4-oxobutenamides 1 were subjected to rhodium-catalyzed conjugate addition with arylboronic acids providing high regio- and enantioselectivity (97:3 to >99:1, >96% ee) and moderate to excellent yields (54−99%). The key to high selectivity is the use of sterically demanding P-chiral diphosphines, such as Tangphos or Duanphos. The product oxobutanamides 2 may be converted to alternate targets by selective derivatization of either the amide or ketone functional group. A stereochemical model predicting the absolute sense of induction was developed based on single-crystal X-ray structures of product and precatalyst.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo701682c