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N-Trimethylsilyloxyenamines as new aldehyde enolate synthons: general, efficient and diastereoselective aldol reaction with ketals and acetals
- 1.0342453 - ÚOCHB 2011 RIV GB eng J - Journal Article
Sonawane, Manoj R. - Císařová, I. - Lyapkalo, Ilya
N-Trimethylsilyloxyenamines as new aldehyde enolate synthons: general, efficient and diastereoselective aldol reaction with ketals and acetals.
Chemical Communications. Roč. 46, č. 15 (2010), s. 2656-2658. ISSN 1359-7345. E-ISSN 1364-548X
Institutional research plan: CEZ:AV0Z40550506
Keywords : N-Trimethylsilyloxyenamines * aldol reaction * diastereoselectivity * Trimethylsilyl trifluoromethanesulfonate
Subject RIV: CC - Organic Chemistry
Impact factor: 5.787, year: 2010
E-N-Trimethylsilyloxyenamines, easily accessible from aldonitrones, proved to be excellent nucleophiles in TMSOTfinduced diastereoselective aldol reaction, both with ketals and acetals, proceeding via an extended transition state and leading to a new aldol C–C-bond in the aldonitrone products, that can be readily hydrolysed to the corresponding aldehydes.
Permanent Link: http://hdl.handle.net/11104/0185185
Number of the records: 1