Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex. Issue 45 (28th November 2017)

• Record Type: Journal Article
• Authors: Yanagisawa, Akira; Yang, Nan; Bamba, Kentaro
• Is Part Of: European journal of organic chemistry. Issue 45(2017)
• Page Start: 6614
• Page End: 6618
• Publication Date: 2017-11-28
• Subjects: Aldehydes -- Allylation -- Asymmetric catalysis -- Ketones -- Silver; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201701177
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP· AgBF4 [BINAP = 2, 2′‐bis(diphenylphosphino)‐1, 1′‐binaphthyl] complex as the chiral precatalyst and triethylamine as the base precatalyst in the presence of 2, 2, 2‐trifluoroethanol. Optically active homoallylic alcohols with up to 95 % ee were obtained in moderate to high yields through the in situ generated chiral allyl silver catalyst. Abstract : An efficient, catalytic, enantioselective allylation reaction of aldehydes or ketones with allyltrimethoxysilane is described. The use of an in situ generated chiral silver alkoxide as the chiral catalyst enables the synthesis of nonracemic homoallylic alcohols with up to 95 % ee . BINAP = 2, 2′‐bis(diphenylphosphino)‐1, 1′‐binaphthyl.