Direct asymmetric aldol reactions catalyzed by (4R)-4-(beta-Naphthalenyl)methoxy-(S)-proline.
A novel proline derivative, (4R)-4-(beta-Naphthalenyl)methoxy-(S)-proline, was conveniently prepared from the naturally occurring (4S)-hydroxy-(S)-proline; 5 mol % of this compound efficiently catalyzes the asymmetric aldol reactions of various benzaldehydes with acetone in excess of acetone as the solvent, giving the aldol adducts in good yields with ee up to 89.8%.
Shen
Zongxuan
Z
Key Laboratory of Organic Synthesis Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, 1 Shizi Street, Suzhou 215006, PR China.
Chen
Wuhong
W
Jiang
Hong
H
Ding
Yi
Y
Luo
Xiaoqing
X
Zhang
Yawen
Y
D000096:Acetone; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
C514364:4-(beta-naphthalenyl)methoxyproline; D000447:Aldehydes; D009281:Naphthalenes; D000096:Acetone; C116609:3-hydroxybutanal; D011392:Proline