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Direct enantioselective vinylogous Mannich‐type reactions of acyclic enals: New experimental insights into the E/Z ‐dilemma

Authors :
Andrea Menichetti
Mauro Pineschi
Sebastiano Di Pietro
Valeria Di Bussolo
Fabio Marchetti
Gennaro Pescitelli
Michela Vargiu
Lucilla Favero
Source :
Chirality. 31:522-533
Publication Year :
2019
Publisher :
Wiley, 2019.

Abstract

The direct heterofunctionalization of acyclic α,β-unsaturated aldehydes with N-acylquinolinium ions contemplating the formation of two stereocentres is studied using dienamine catalysis. This work gives some new experimental insights on the remote stereocontrol in dienamine catalysis using unbiased aliphatic systems and large electrophiles, pointing to a (Z)-preference of the reactive configuration of the second double bond.

Details

ISSN :
1520636X and 08990042
Volume :
31
Database :
OpenAIRE
Journal :
Chirality
Accession number :
edsair.doi.dedup.....5ffa72caac6c53726c50ec68efd17ba5
Full Text :
https://doi.org/10.1002/chir.23077