Ein neuartiger chiraler Synthesebaustein mit Neopentangerüst: Chemo‐enzymatische Darstellung von ( R )‐CH 3 C(CH 2 OSO 2 CF 3 )(CH 2 Cl)(CH 2 Br)

Autor:	Günter Helmchen, Rainer Vogel, Horst Heidel, Gottfried Huttner
Rok vydání:	1994
Předmět:	Inorganic Chemistry Carboxylic Ester Hydrolases chemistry.chemical_compound Hydrolysis Neopentane Chemistry Stereochemistry Enantioselective synthesis Esterase Pig liver
Zdroj:	Chemische Berichte. 127:271-274
ISSN:	0009-2940
DOI:	10.1002/cber.19941270138
Popis:	A Novel Chiral Building Block with Neopentane Framework for Synthesis: Chemo-Enzymatic Preparation of (R)-CH3C(CH2OSO2CF3)(CH2Cl)(CH2Br) The pig liver esterase (PLE) catalysed hydrolysis of the prochiral malonic ester (BzlOCH2)(Me)C(COOMe)2 (1) leads to its chiral monoester 2 in selectivities up to 81% ee. Compound 2 is an ideal entry point for the enantioselective synthesis of 1,1′,1″-substituted neopentanes CH3C(CH2X)-(CH2Y)(CH2Z) with three different leaving groups, X, Y, and Z. CH3C(CH2OSO2CF3)(CH2Br)(CH2Cl) (8) is a versatile reactive building block for the asymmetric synthesis of compounds containing the neopentane-C5 skeleton.
Databáze:	OpenAIRE
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