Small peptides catalyze highly enantioselective direct aldol reactions of aldehydes with hydroxyacetone: unprecedented regiocontrol in aqueous media.
[reaction: see text] L-Proline-based small peptides have been developed as efficient catalysts for the asymmetric direct aldol reactions of hydroxyacetone with aldehydes. Chiral 1,4-diols 7, which are disfavored products in similar aldol reactions catalyzed by either aldolases or L-proline, were obtained in high yields and enantioselectivities of up to 96% ee with peptides 3 and 4 in aqueous media.
Tang
Zhuo
Z
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province and Union Laboratory of Asymmetric Synthesis, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
Yang
Zhi-Hua
ZH
Cun
Lin-Feng
LF
Gong
Liu-Zhu
LZ
Mi
Ai-Qiao
AQ
Jiang
Yao-Zhong
YZ
D000096:Acetone / Q000031:analogs & derivatives* / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000595:Amino Acid Sequence; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water
D000447:Aldehydes; D001547:Benzaldehydes; D010455:Peptides; D014867:Water; D000096:Acetone; C029915:4-nitrobenzaldehyde; C004433:acetol; C116609:3-hydroxybutanal; D011392:Proline