Abstract
A Mannich-aza-Michael reaction in which both an electrophile and a nucleophile are activated provides a simple, highly enantioselective route to isoquinuclidines (1) from imines (2) and cyclohexenone (3). A feature of the reaction is the interplay of an achiral and a chiral Brønsted acid, which enable the asymmetric reaction process by cooperative activation of the enone and the imine. (Chemical Equation Presented).
Original language | English (US) |
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Pages (from-to) | 7832-7835 |
Number of pages | 4 |
Journal | Angewandte Chemie - International Edition |
Volume | 45 |
Issue number | 46 |
DOIs | |
State | Published - Nov 27 2006 |
Externally published | Yes |
Keywords
- Asymmetric synthesis
- Ion pairs
- Isoquinuclidines
- Mannich bases
- Michael addition
ASJC Scopus subject areas
- Catalysis
- General Chemistry