Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 1, Pages 46-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja076802c
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Funding
- NIDDK NIH HHS [DK38226, P01 DK038226, P01 DK038226-220006] Funding Source: Medline
- NIGMS NIH HHS [GM31278, R01 GM031278-24, R01 GM031278] Funding Source: Medline
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An organocatalytic, enantioselective oxy-Michael addition to achiral gamma- and delta-hydroxy-alpha, beta-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral beta-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction.
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