1394046-53-7Relevant articles and documents
Synthesis of optically active 4-substituted 2-cyclohexenones
Houjeiry, Tania I.,Poe, Sarah L.,McQuade, D. Tyler
, p. 4394 - 4397 (2012/10/29)
Recently, Nicolaou and Baran independently synthesized optically active 4-substituted 2-cyclohexenones via an efficient LiOH-mediated intramolecular aldol condensation. Thus far, application of their cyclization approach has been limited to ketoaldehydes where the R-group is branched. It is demonstrated that the LiOH-mediated cyclization, when applied to substrates containing unbranched R-groups, results in significant erosion of optical purity. A mechanistic justification is provided, and a set of neutral, organocatalyzed conditions is identified that enables cyclization with little loss in optical purity.