Enantioselective acylation using a second-generation P-aryl-2-phosphabicyclo[3.3.0]octane catalyst

The Journal of Organic Chemistry
J A MacKay, E Vedejs

Abstract

The synthesis of P-aryl-2-phosphabicylco[3.3.0]octane x HBF4 salts 3a and 3c is described. Incorporation of the P-3,5-di-tert-butyl-4-methoxyphenyl group in 3c allows use of a less expensive aryl bromide starting material. Deprotonation of the air-stable salts in situ with triethylamine releases the corresponding phosphines 1a and 1c for use in the kinetic resolution of representative secondary alcohols. The method is convenient for small-scale experiments and affords enantioselectivities s close to the values obtained using the free phosphines 1a and 1b in cases where s is ca. 40 or lower.

References

Jul 13, 2000·Accounts of Chemical Research·G C Fu
Feb 17, 2001·Organic Letters·E Vedejs, J A MacKay
Apr 3, 2003·Journal of the American Chemical Society·Edwin Vedejs, Olafs Daugulis
Sep 1, 1947·Journal of the American Chemical Society·C O BADGETT

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Citations

Jul 1, 2011·Organic Letters·Cody I SheppardSheryl L Wiskur
Feb 12, 2011·Physical Chemistry Chemical Physics : PCCP·Boris Maryasin, Hendrik Zipse
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Jun 22, 2011·Angewandte Chemie·Christian E Müller, Peter R Schreiner
Sep 26, 2012·Chemical Society Reviews·Alvaro Enríquez-García, E Peter Kündig
Jun 19, 2010·The Journal of Organic Chemistry·Trisha A DuffeyEdwin Vedejs
Sep 28, 2018·Chemical Reviews·Hongchao GuoOhyun Kwon
Feb 22, 2008·Journal of the American Chemical Society·Yin WeiHendrik Zipse

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