Premium
Asymmetric Intramolecular Ene Reaction Catalyzed by a Chiral Titanium Reagent and Synthesis of (—)‐ε‐Cadinene
Author(s) -
Narasaka Koichi,
Hayashi Yujiro,
Shimada Satoru,
Yamada Jun
Publication year - 1991
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.199100030
Subject(s) - chemistry , intramolecular force , cyclohexanone , cyclopentanone , ene reaction , reagent , catalysis , diol , titanium , organic chemistry , combinatorial chemistry , polymer chemistry
A highly diastereo‐ and enantio‐selective intramolecular ene reaction was developed by employing a chiral titanium reagent generated in situ from TiCl 2 (OPr i ) 2 and a tartrate‐derived chiral 1,4‐diol. This reaction afforded masked cyclohexanone and cyclopentanone derivatives with high optical purities which were synthetically useful chiral building blocks. From the intramolecular ene product (—)‐ε‐cadinene was synthesized by the use of the newly developed intramolecular Michael reaction.