Preparation of new chiral bisoxazoline ligands for the catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto phenyl sulfone to afford a useful bicyclo[3.1.0]hexane derivative

Takashi Sawada, Masahisa Nakada*

*この研究の対応する著者

研究成果: Article査読

24 被引用数 (Scopus)

抄録

Herein we describe the preparation of novel chiral bisoxazoline ligands with various substituents at the bisoxazoline linkage, for use in the catalytic asymmetric intramolecular cyclopropanation (CAIMCP) of α-diazo-β-keto phenyl-5-hexenyl sulfone to afford a simple, but useful, bicyclo[3.1.0]hexane derivative. The enantioselectivity of the CAIMCP of α-diazo-β-keto phenyl-5-hexenyl sulfone was improved and a product with 84% ee was obtained using 30 mol % of the catalyst, which was prepared in situ by CuOTf and the new bisoxazoline ligand with two 3,5-di-tert-butylbenzyl groups at the bisoxazoline linkage. The product was obtained in enantiomerically pure form by a single crystallization, enabling its use as a chiral building block.

本文言語English
ページ(範囲)350-356
ページ数7
ジャーナルTetrahedron Asymmetry
23
5
DOI
出版ステータスPublished - 2012 3月 15

ASJC Scopus subject areas

  • 触媒
  • 物理化学および理論化学
  • 有機化学
  • 無機化学

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