Tetrahedron Letters

An efficient chemo-enzymatic approach to the enantioselective synthesis of 2-methyl-1, 3-propamedical derivatives

E Santaniello, P Ferraboschi, P Grisenti

Index: Santaniello, Enzo; Ferraboschi, Patrizia; Grisenti, Paride Tetrahedron Letters, 1990 , vol. 31, # 39 p. 5657 - 5660

Full Text: HTML

Citation Number: 50

Abstract

Abstract Lipase-catalyzed transesterification of 2-methyl-1, 3-propanediol 1 in chloroform affords enantiomerically pure (S)-(−)-acetate 2, from which the (R)-(+)-silyl ethers 4a-b can be efficiently prepared (> 98% ee). The (S)-TBDPS derivative 4b could be also efficiently and enantioselectively prepared by the same enzymatic procedure, starting from racemic 5b.

Related Articles:

Enantiotopically selective oxidation of. alpha.,. omega.-diols with enzyme systems of microorganisms

[Ohta, Hiromichi; Tetsukawa, Hatsuki; Noto, Naoko Journal of Organic Chemistry, 1982 , vol. 47, # 12 p. 2400 - 2404]

Ring-opening of 2, 3-epoxy-1-propanol with R 3 Al: Unprecedented regiochemical switching simply achieved by changing alkyl substituents of aluminium reagent

[Journal of Organometallic Chemistry, , vol. 690, # 16 p. 3697 - 3699]

Hydrocarbonylation of prop-2-en-1-ol to butane-1, 4-diol and 2-methylpropan-1-ol catalysed by rhodium triethylphosphine complexes

[Journal of the Chemical Society - Dalton Transactions, , # 9 p. 1793 - 1800]

Hydroboration. 57. Hydroboration with 9-borabicyclo [3.3. 1] nonane of alkenes containing representative functional groups

[Journal of Organic Chemistry, , vol. 46, # 20 p. 3978 - 3988]

More Articles...