Issue 22, 2003
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective alkaloid synthesis via ene-type cyclizations catalyzed by cationic chiral palladium(ii) complexes of PN-ligands with an achiraloxazoline unit†

Manabu Hatano‡a  and  Koichi Mikami*a  

* Corresponding authors

a Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, O-okayama, Tokyo 152-8552, Japan
E-mail: kmikami@o.cc.titech.ac.jp
Fax: +81-3-5734-2776
Tel: +81-3-5734-2142

Abstract

A highly efficient asymmetric alkaloid synthesis via ene-type cyclizations catalyzed by cationic chiral palladium(II) complexes of PN-ligands with an achiral gem-dimethyl oxazoline unit is shown to give 5-membered products with a quaternary carbon center, including a spiro-amide, almost quantitatively with extremely high enantiomeric excesses.

Graphical abstract: Highly enantioselective alkaloid synthesis via ene-type cyclizations catalyzed by cationic chiral palladium(ii) complexes of PN-ligands with an achiral oxazoline unit

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Article information

DOI
https://doi.org/10.1039/B305865B
Article type
Communication
Submitted
23 May 2003
Accepted
17 Sep 2003
First published
26 Sep 2003

Org. Biomol. Chem., 2003,1, 3871-3873

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Highly enantioselective alkaloid synthesis via ene-type cyclizations catalyzed by cationic chiral palladium(II) complexes of PN-ligands with an achiral oxazoline unit

M. Hatano and K. Mikami, Org. Biomol. Chem., 2003, 1, 3871 DOI: 10.1039/B305865B

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