Enantioselective Catalysis of Intramolecular Morita-Baylis-Hillman and Related Reactions by Chiral Rhenium-Containing Phosphines of the Formula (η 5 -C 5 H 5 )Re(NO)(PPh 3 )(CH 2 PAr 2 ) Academic Article uri icon

abstract

  • The racemic rhenium-containing phosphine (η5-C 5H5)Re(NO)(PPh3)(CH2PPh 2) catalyzes intramolecular Morita-Baylis-Hillman reactions of four R(CO)CH=CH(CH2)nCH2CHO species (n = 1 or 2; R = Ph, S-i-Pr, p-Tol, Me) in benzene or chlorobenzene at 20°C. The products R(CO)CH=CH(CH2)nCH2CHOH are isolated in 88-99% yields and 38-74% ee when enantiopure S-configured catalyst is used. Similar reactions of R(CO)CH=CHCH2CH2CH=CH(CO)R (R = Ph, S-i-Pr) give R(CO)C=CHCH2CH2CHCH2(CO)R in 63-87% yields and 42-56% ee. © Georg Thieme Verlag Stuttgart.

author list (cited authors)

  • Seidel, F., & Gladysz, J.

citation count

  • 2

publication date

  • April 2007