Enantioselective Addition of Methallyl- and Crotyltins to Aldehydes Catalyzed by BINAP·Ag(I) Complex

Synlett

Volumn 1997, Issue 1, 1997, Pages 88-90

  Yanagisawa, Akira ^a   Ishiba, Atsushi ^a   Nakashima, Hiroshi ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001936390     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0030-1258388     Document Type: Article

References (31)

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28. The absolute configuration of the syn-isomer is tentatively shown as 1R, 2S.
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30. 2 However, the transmetallation pathway cannot be excluded entirely since the recovered crotyltributyltin was found to be slightly isomerized: for example, reaction of 1 equiv of (Z)-crotyltributyltin (E/Z = 7/93) with benzaldehyde (1 equiv) in the presence of 20 mol % of (R)-BINAP·AgOTf in THF at -20 ∼ 20 °C for 24 h afforded a mixture of homoallylic alcohols in 30% combined yield with an anti/syn ratio of 86/14 and a 14:86 mixture of (E)- and (Z)-crotyltin was recovered in 47% yield. The enantioselectivities of the anti- and syn-isomers were 94% ee and 65% ee, respectively.
31. W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz and R. L. Halterman, J. Am. Chem. Soc., 1990, 112, 6339.