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Synfacts 2008(3): 0313-0313
DOI: 10.1055/s-2008-1042726
DOI: 10.1055/s-2008-1042726
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York
α-Vinylation of Aldehydes
H. Kim, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
Further Information
Publication History
Publication Date:
21 February 2008 (online)
Significance
An asymmetric α-vinylation of aldehydes is described. Under mild oxidative conditions, commercially available chiral secondary amine catalyst 1 ×TFA converts a wide range of aldehydes 2 with functional groups such as aromatic rings, olefins, benzyl ethers, and carbamates into α-(E)-vinyl aldehydes 3. A broad scope of vinyl trifluoroborate salts 4, including para-substituted styryl systems with electron-withdrawing, -neutral and -donating groups, are tolerated as vinyl coupling partners. Good yields are reported alongside excellent enantioselectivities and, excellent trans-olefin selectivity.