Efficient one-step aldol-type reaction of ketones with acetals and ketals mediated by dibutylboron triflate/diisopropylethyl amine. Academic Article uri icon

Overview

abstract

  • one-step Mukaiyama aldol type reaction [reaction: see text] A highly efficient one-step Mukaiyama aldol-type reaction has been developed for the synthesis of beta-alkoxy carbonyl compounds starting from ketones and acetals/ketals. The reaction is mediated by a combination of Bu(2)BOTf and i-Pr(2)NEt affording the products in high yields. Formation of the two possible diastereoisomers of the beta-alkoxy ketones from the chiral acetals shows that the condensation takes place by an S(N)1 mechanism, involving prior opening of the acetal to an oxonium ion.

publication date

  • January 8, 2004

Identity

Digital Object Identifier (DOI)

  • 10.1021/ol030108u

PubMed ID

  • 14703367

Additional Document Info

volume

  • 6

issue

  • 1