Palladium-catalyzed asymmetric decarboxylative lactamization of gamma-methylidene-delta-valerolactones with isocyanates: conversion of racemic lactones to enantioenriched lactams

Ryo Shintani; Soyoung Park; Fumitaka Shirozu; Masataka Murakami; Tamio Hayashi

doi:10.1021/ja807662b

Palladium-catalyzed asymmetric decarboxylative lactamization of gamma-methylidene-delta-valerolactones with isocyanates: conversion of racemic lactones to enantioenriched lactams

J Am Chem Soc. 2008 Dec 3;130(48):16174-5. doi: 10.1021/ja807662b.

Authors

Ryo Shintani¹, Soyoung Park, Fumitaka Shirozu, Masataka Murakami, Tamio Hayashi

Affiliation

¹ Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan. [email protected]

PMID: 18998676
DOI: 10.1021/ja807662b

Abstract

A palladium-catalyzed asymmetric decarboxylative reaction of racemic gamma-methylidene-delta-valerolactones with aryl isocyanates has been developed to give enantioenriched 3,3-disubstituted 2-piperidones. High enantioselectivity has been achieved by tuning the ester group on substrate and the substituents of phosphoramidite ligand.