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Enantioselective Protonation of a Simple Enol: Aminoalcohol‐Catalyzed Ketonization of a Photochemically Produced 2‐Methylinden‐3‐ol
Author(s) -
Henin Franpise,
Muzart Jacques,
Pete JeanPierre,
M'boungouM'passi Anastase,
Rau Hermann
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199104161
Subject(s) - enol , protonation , enantioselective synthesis , ketone , catalysis , chemistry , keto–enol tautomerism , organic chemistry , scope (computer science) , photochemistry , medicinal chemistry , computer science , ion , programming language
The enol 2, produced by a Norrish type II photoelimination from 1 , is protonated enantioselectively to ketone 3 in the presence of (–)‐ephedrine. Best optical yields are obtained at 0 o C using small amounts of the chiral aminoalcohol. There is still wide scope for optimization.