Diastereoselective synthesis of a highly functionalized cyclohexene embedded with a quaternary stereogenic centre by self Diels-Alder dimerization of a [3]dendralene attached to a (-)-menthol auxiliary

作者：Singh Rekha; Ghosh Sunil K^*

来源：Tetrahedron: Asymmetry , 2014, 25(1): 57-62.

DOI：10.1016/j.tetasy.2013.11.005

A novel route to a chiral functionalized [3]dendralene attached to a (-)-menthol auxiliary has been developed, which involves a dimethylsulfonium methylide mediated olefination of a substituted ethenylidene phosphonoacetate (-)-menthyl ester, followed by a Horner-Wordsworth-Emmons reaction with 4-bromobenzaldehyde. The chiral [3]dendralene was reactive enough to undergo intermolecular Diels-Alder cyclodimerization to give the highly substituted cyclohexene with very high regio- and diastereoselectivity.

• 出版日期2014-1-15