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Metal-Free Regiodivergent Addition of Carbon Nucleophiles to ?,?-Unsaturated Electrophiles.

ABSTRACT: A mild and metal-free regiodivergent addition of carbon nucleophiles to ?,?-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to ?,?-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and ?,?-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity.

SUBMITTER: Spitz C

PROVIDER: S-EPMC6152382 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Metal-Free Regiodivergent Addition of Carbon Nucleophiles to α,β-Unsaturated Electrophiles.

Spitz Cédric C Giuglio-Tonolo Alain G AG Terme Thierry T Vanelle Patrice P

Molecules (Basel, Switzerland) 20170714 7

A mild and metal-free regiodivergent addition of carbon nucleophiles to α,β-unsaturated electrophiles was developed. Total 1,2-regioselectivity was observed in the addition of nitrobenzyl chloride derivative 1 to α,β-unsaturated aldehydes 2 in the presence of TDAE. Moreover, the reaction between p-nitrobenzyl chloride 1a and α,β-unsaturated iminium salts 4 led to the formation of the 1,4-adduct with total regioselectivity. ...[more]

PMID: 28708088

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