Asymmetric synthesis of gamma-hydroxy alpha-enones by 1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed stereoselective rearrangement of chiral alpha-sulfinyl enones

Motofumi Miura; Masaharu Toriyama; Takashi Kawakubo; Ken Yasukawa; Toshio Takido; Shigeyasu Motohashi

doi:10.1021/ol1015724

Asymmetric synthesis of gamma-hydroxy alpha-enones by 1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed stereoselective rearrangement of chiral alpha-sulfinyl enones

Org Lett. 2010 Sep 3;12(17):3882-5. doi: 10.1021/ol1015724.

Authors

Motofumi Miura¹, Masaharu Toriyama, Takashi Kawakubo, Ken Yasukawa, Toshio Takido, Shigeyasu Motohashi

Affiliation

¹ School of Pharmacy, Nihon University, 7-7-1, Narashinodai, Funabashi-shi, Chiba 274-8555, Japan. miura.motofumi@nihon-u.ac.jp

PMID: 20704185
DOI: 10.1021/ol1015724

Abstract

The asymmetric rearrangement of optically active alpha-sulfinyl enone 1 induced by catalytic DBU and triphenylphosphine gave optically active gamma-hydroxy alpha-enone derivatives (up to 99% ee) in good yield following treatment with aqueous hydrogen peroxide.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Aza Compounds / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Hydrogen Peroxide / chemistry
Ketones / chemical synthesis*
Ketones / chemistry
Molecular Structure
Stereoisomerism
Sulfoxides / chemistry*

Substances

Aza Compounds
Bridged Bicyclo Compounds, Heterocyclic
Ketones
Sulfoxides
Hydrogen Peroxide