Lipase-catalyzed desymmetrization of quaternary carbon-containing 1,3-propanediols: A new entry to the asymmetric synthesis of α-substituted serine analogues

Synlett

Volumn , Issue 8, 2006, Pages 1201-1204

  Tian, Ping ^a   Xu, Ming Hua ^b   Wang, Zhi Qian ^a   Li, Zu Yi ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

substituted serine; 2 nitropropane 1,3 diols; Desymmetrization; Lipase catalyzed

Indexed keywords

1,3 PROPANEDIOL; 2 BENZYL 2 NITROPROPANE 1,3 DIOL; 2 NITROPROPANE; CARBON; SERINE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; ESTERIFICATION; ROOM TEMPERATURE; SYNTHESIS;

EID: 33744462855     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939713     Document Type: Article

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26. 5: C, 56.91; H, 5.97; N, 5.53. Found: C, 56.96; H, 5.81; N, 5.65.
27. We attempted to use 2-NHBoc- and 2-NHAc-substituted 1,3-diols as substrates instead of 2-nitropropane-1,3-diol, however, esterification in the presence of PPL gave very poor yields.
28. 2 = 0.2517.
29. 6Na: 390.1887; found: 390.1892.
30. 6H: 338.1604; found: 338.1602.
31. 5H: 294.1347; found: 294.1351.