Literature DB >> 23548074

Diastereoselective reaction of sulfoxonium ylides, aldehydes and ketenes: an approach to trans-γ-lactones.

Mukulesh Mondal1, Han-Jen Ho, Nicholas J Peraino, Melanie A Gary, Kraig A Wheeler, Nessan J Kerrigan.   

Abstract

In this paper, a novel approach to γ-lactones from the reaction of sulfoxonium ylides, aldehydes, and ketenes is described. The new ylide-based method provides access to γ-lactones from disubstituted ketenes, in good yields, and with good diastereoselectivity favoring the trans-diastereomer (11 examples with dr ≥ 82:18, dr up to 92:8).

Entities:  

Mesh:

Substances:

Year:  2013        PMID: 23548074     DOI: 10.1021/jo4003213

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts.

Authors:  Nicholas J Peraino; Sven H Kaster; Kraig A Wheeler; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-12-09       Impact factor: 4.354

Review 2.  Recent Developments in Vinylsulfonium and Vinylsulfoxonium Salt Chemistry.

Authors:  Mukulesh Mondal; Shi Chen; Nessan J Kerrigan
Journal:  Molecules       Date:  2018-03-23       Impact factor: 4.411

  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.