Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/92972
Title: A novel and general α-regioselective and highly enantioselective prenylation of aldehydes
Authors: Cheng, H.-S.
Loh, T.-P. 
Issue Date: 30-Apr-2003
Source: Cheng, H.-S.,Loh, T.-P. (2003-04-30). A novel and general α-regioselective and highly enantioselective prenylation of aldehydes. Journal of the American Chemical Society 125 (17) : 4990-4991. ScholarBank@NUS Repository.
Abstract: This communication describes a novel and general method for the α-regioselective prenylation of carbonyl compounds. This method which employs chiral γ-prenyl-1,5 diol as the prenyl source using a catalytic amount of Lewis or Brønsted acid affords the products in excellent enantioselectivies (up to 98% ee) and good yields (up to 95% yield). Furthermore, the reaction is highly chemoselective, reacting selectively with the aldehyde without affecting the enone and the α,β-unsaturated ester functionalities. Detailed mechanistic studies disclose the facile epimerization of aromatic alcohol in dichloromethane in the presence of In(OTf)3. The use of non-polar solvents such as hexane in the presence of In(OTf)3 or TfOH effectively suppresses this epimerization. Copyright © 2003 American Chemical Society.
Source Title: Journal of the American Chemical Society
URI: http://scholarbank.nus.edu.sg/handle/10635/92972
ISSN: 00027863
Appears in Collections:Staff Publications

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