Enantioselective Organocatalytic Conjugate Addition of Aldehydes to Vinyl Sulfones and Vinyl Phosphonates as Challenging Michael Acceptors
| Autor: | Gérald Bernardinelli, Alexandre Alexakis, Yaroslav Filinchuk, Sarah Sulzer-Mossé, Jiri Mareda, Guillaume Bollot |
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| Rok vydání: | 2009 |
| Předmět: |
inorganic chemicals
Pyrrolidines Vinyl Compounds Organophosphonates Catalysis Pyrrolidine chemistry.chemical_compound Michael addition Combinatorial Chemistry Techniques Organic chemistry heterocyclic compounds Sulfones Amines Enantiomeric excess Aldehydes Molecular Structure Organocatalysis organic chemicals Organic Chemistry technology industry and agriculture Enantioselective synthesis Asymmetric synthesis Stereoisomerism General Chemistry Models Chemical chemistry ddc:540 Michael reaction Conjugate |
| Zdroj: | Chemistry-A European Journal, Vol. 15, No 13 (2009) pp. 3204-3220 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.200801892 |
| Popis: | Chiral framework: Chiral amines with pyrrolidine frameworks catalyze the enantioselective conjugate addition of a wide range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to99 % ee (see scheme). The high versatility of the Michael adducts is exemplified by various functionalizations with conservation of the optical purity.Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to99 % ee. This novel process provides synthetically useful chiral gamma-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail. |
| Databáze: | OpenAIRE |
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