Please use this identifier to cite or link to this item:
|Title:||A novel and general α-regioselective and highly enantioselective prenylation of aldehydes||Authors:||Cheng, H.-S.
|Issue Date:||30-Apr-2003||Citation:||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|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Oct 12, 2019
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.