Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen

Xiao-Fei Yang; Chang-Hua Ding; Xiao-Hui Li; Jian-Qiang Huang; Xue-Long Hou; Li-Xin Dai; Pin-Jie Wang

doi:10.1021/jo301506p

Regio- and enantioselective palladium-catalyzed allylic alkylation of nitromethane with monosubstituted allyl substrates: synthesis of (R)-rolipram and (R)-baclofen

J Org Chem. 2012 Oct 19;77(20):8980-5. doi: 10.1021/jo301506p. Epub 2012 Oct 1.

Authors

Xiao-Fei Yang¹, Chang-Hua Ding, Xiao-Hui Li, Jian-Qiang Huang, Xue-Long Hou, Li-Xin Dai, Pin-Jie Wang

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China.

PMID: 22992268
DOI: 10.1021/jo301506p

Abstract

The Pd-catalyzed asymmetric allylic alkylation (AAA) reaction of nitromethane with monosubstituted allyl substrates was realized for the first time to provide corresponding products in high yields with excellent regio- and enantioselectivities. The protocol was applied to the enantioselective synthesis of (R)-baclofen and (R)-rolipram.

Publication types

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

MeSH terms

Alkylation
Allyl Compounds / chemistry*
Baclofen / chemical synthesis*
Baclofen / chemistry
Catalysis
Methane / analogs & derivatives*
Methane / chemistry
Molecular Structure
Nitroparaffins / chemistry*
Organometallic Compounds / chemistry*
Palladium / chemistry*
Rolipram / chemical synthesis*
Rolipram / chemistry
Stereoisomerism

Substances

Allyl Compounds
Nitroparaffins
Organometallic Compounds
Palladium
Baclofen
Rolipram
Methane
nitromethane