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Enantioselektive Verseifung der Diacetate von 2‐Nitro‐1,3‐diolen mit Schweineleber‐Esterase und Herstellung enantiomerenreiner Derivate von 2‐Nitro‐allylalkoholen (chirale Verknüpfungsreagenzien)
Author(s) -
Eberle Martin,
Egli Martin,
Seebach Dieter
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710102
Subject(s) - chemistry , saponification , nitro , allylic rearrangement , enantioselective synthesis , enantiomeric excess , reagent , organic chemistry , enantiomer , stereochemistry , medicinal chemistry , alkyl , catalysis
Enantioselective Saponification of Diacetates of 2‐Nitro‐1,3‐propanediols by Pig‐Liver Esterase and Preparation of Enantiomerically Pure Derivatives of 2‐Nitro‐allylic Alcohols (Chiral Multiple‐Coupling Reagents) The reproducible enantioselective saponification of open‐chain and cyclic diacetates of meso ‐2‐nitro‐1,3‐propanediols (see 4b – 13b ) with pig‐liver esterase (PLE) gives monoacetates (see 4c – l3c ) of > 95% enantiomeric excess. The Re enantiotopic acetate group appears to be saponified preferentially, as proved by the X‐ray crystal structure analysis of three camphanoates 4d , 6d , and 7d . Elimination of H 2 O or AcOH from the hydroxy acetates thus available gives derivatives of nitro‐allylic alcohols (see 20 – 24 , 27 , and 29 ) which are subjected to diastereoselective Michael additions or S N 2′ substitutions.