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Chiral Primary Amine Catalyzed Asymmetric Direct Cross‐Aldol Reaction of Acetaldehyde
Author(s) -
Hu Shenshen,
Zhang Long,
Li Jiuyuan,
Luo Sanzhong,
Cheng JinPei
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100267
Subject(s) - chemistry , acetaldehyde , aldol reaction , catalysis , yield (engineering) , amine gas treating , isatin , malononitrile , derivative (finance) , primary (astronomy) , organic chemistry , vicinal , aqueous solution , combinatorial chemistry , ethanol , materials science , physics , astronomy , financial economics , economics , metallurgy
Abstract The first primary aminocatalytic direct cross‐aldol reaction of acetaldehyde is presented. Among the various vicinal diamines screened, the L ‐ tert ‐leucine derivative 1c in conjunction with (H 4 SiW 12 O 40 ) 0.25 was identified as the optimal catalyst; good catalytic activity (up to 99 % yield in 4 h), and high enantioselectivities (up to 92 % ee ) were achieved for a range of donors, including aromatic aldehydes and isatin derivatives. Aqueous acetaldehyde solution and paraldehyde can be conveniently applied in this system.