Synfacts 2010(8): 0952-0952  
DOI: 10.1055/s-0030-1257800
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Vinylogous Mukaiyama Aldol Reactions

Contributor(s): Benjamin List, Lars Ratjen
N. Zhu, B.-C. Ma*, Y. Zhang, W. Wang*
Lanzhou University, P. R. of China
Further Information

Publication History

Publication Date:
22 July 2010 (online)

Significance

An organocatalytic vinylogous ­Mukaiyama aldol reaction (VMAR) of aromatic ­aldehydes with 2-(trimethylsilyloxy)furan is reported. The employed catalyst having a bifunctional ­quinine-based skeleton with an adjacent thiourea moiety furnished the desired substituted γ-buten-olides in good yields and diastereoselectivities and with high optical purities.

Review: S. E. Denmark, J. R. Heemstra Jr., G. L. Beutner Angew. Chem. Int. Ed. 2005, 44, 4682-4698.