NDLI: Organocatalysis with cysteine derivatives: recoverable and cheap chiral catalyst for direct aldol reactions

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Organocatalysis with cysteine derivatives: recoverable and cheap chiral catalyst for direct aldol reactions

Content Provider	Springer Nature Link
Author	Li, Shi Fu, Xiangkai Wu, Chuanlong
Copyright Year	2011
Abstract	Highly enantioselective, recoverable and cheap cysteine derivatives have been developed with improved solubility properties in common, nonpolar organic solvents. The reactions were catalyzed using 5 mol% 1e, and the aldol products could be obtained with up to 99:1 syn/anti ratio and >99% ee. The catalyst could be easily recovered and reused, with only a slight decrease of enantioselectivity observed for five cycles. Catalyst 1e can be efficiently used in large-scale reactions with enantioselectivity being maintained at the same level, which offers great possibility for application in industry.(i) Direct aldol reactions proceeded in 1,2-dichloroethane using simple procedures. (ii) Direct S-acylation of cysteine to give organocatalysts 1a–f can be economically carried out easily in a single step from commercially available sources, with both enantiomers being readily available. (iii) 5 mol% catalyst 1e was sufficient to furnish the aldol products in excellent yields (up to 93%) and enantioselectivities (up to 99%). (iv) Catalyst 1e could be easily recovered and reused, and also can be efficiently used in large-scale reactions with enantioselectivity being maintained at the same level, which offers great possibility for applications in industry.
Starting Page	195
Ending Page	205
Page Count	11
File Format	PDF
ISSN	09226168
Journal	Research on Chemical Intermediates
Volume Number	38
Issue Number	1
e-ISSN	15685675
Language	English
Publisher	Springer Netherlands
Publisher Date	2011-06-15
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Cysteine derivatives Aldol reactions Recoverable catalyst Large-scale reactions Inorganic Chemistry Catalysis Physical Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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