Asymmetric Addition of Allylic Stannanes to Aldehydes Catalyzed by BINAPAg(I) Complex

Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP*AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety o...

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Published inBulletin of the Chemical Society of Japan Vol. 74; no. 6; p. 1129
Main Authors Yanagisawa, Akira, Nakashima, Hiroshi, Nakatsuka, Yoshinari, Ishiba, Atsushi, Yamamoto, Hisashi
Format Journal Article
LanguageEnglish
Published Tokyo Chemical Society of Japan 01.06.2001
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Summary:Catalytic asymmetric allylation of aldehydes with allylic trialkylstannanes was achieved with BINAP*AgOTf complex as catalyst. The chiral silver(I) catalyst was readily prepared by stirring an equimolar mixture of BINAP and silver(I) triflate in THF at room temperature. The allylation of a variety of aromatic and α,β-unsaturated aldehydes resulted in high yields and remarkable enantioselectivities. Addition of γ-substituted allylstannanes such as 2-butenyltributylstannane and trialkyl-2,4-pentadienylstannanes exclusively gave γ-adducts. High anti-selectivity was also obtained in the reaction with 2-butenyltributylstannane, irrespective of the configuration at the double bond.
ISSN:0009-2673
1348-0634