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Intermolecular cross-double-michael addition between nitro and carbonyl activated olefins as a new approach in C-C bond formation.

Organic letters (2007-10-04)
Xiaohua Sun, Sujata Sengupta, Jeffrey L Petersen, Hong Wang, James P Lewis, Xiaodong Shi
ABSTRACT

A novel intermolecular cross-double-Michael addition between nitro and carbonyl activated olefins has been developed through Lewis base catalysis. The reaction took place with a large group of beta-alkyl nitroalkenes and alpha,beta-unsaturated ketone/esters, producing an allylic nitro compound in good to excellent yields.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium azide, ReagentPlus®, ≥99.5%
Sigma-Aldrich
Sodium azide, BioXtra
Sigma-Aldrich
Sodium azide, purum p.a., ≥99.0% (T)