@article { ISI:000360398900018, title = {Asymmetric vinylogous michael reaction of cyclic enones with silyloxy furans}, journal = {Chemical Communications}, volume = {51}, number = {73}, year = {2015}, month = {JUL}, pages = {13941-13944}, publisher = {ROYAL SOC CHEMISTRY}, address = {THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND}, abstract = {

The asymmetric vinylogous Michael reaction of cyclohexenone/medium and large cyclic enones with 2-silyloxyfuran is still a synthetic challenge. In this report, we have explored 1,4-conjugate addition of an enantioselective chiral, primary diamine catalyzed, 2-silyloxy furan to various cyclic enones and beta-substituted cyclic enones. The reaction provided syn-Michael adducts (cycloalkane connected gamma-butenolide) with good yields, diastereo and enantioselectivities. Furthermore, the synthetic potential of these syn-Michael adducts is demonstrated by 1,4-addition of nucleophiles on the butenolide substructure.

}, issn = {1359-7345}, doi = {10.1039/c5cc05617a}, author = {Jadhav, Amol P. and Rao, V. U. Bhaskara and Singh, Pradeep and Gonnade, Rajesh G. and Singh, Ravi P.} }