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Utilization of industrial waste materials, 5. Synthesis of new, chiral 1,3,2‐oxazaphospholidine‐borane complexes and attempts to apply them in the stereoselective synthesis
Author(s) -
Peper Viola,
Stingl Klaus,
Thümler Hajo,
Saak Wolfgang,
Haase Detlev,
Pohl Siegfried,
Jugé Sylvain,
Martens Jürgen
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199512298
Subject(s) - borane , chemistry , enantioselective synthesis , catalysis , octane , stereoselectivity , phosphinite , organic chemistry , combinatorial chemistry , medicinal chemistry
New, chiral 1,3,2‐oxazaphospholidine‐borane complexes 3a‐b and 8a‐d were synthesized from the β‐amino alcohols 1a‐b and 6a‐d . The borane complexes 3, 8a, 8c , and 8d were allowed to react with different organolithium compounds and afforded the corresponding aminophosphane‐borane complexes 4a–c and 9a‐g . Acid methanolysis of those complexes led to the formation of the phosphinite‐borane complexes 5a‐c. This is a further example of the utilization of the industrial waste material ( all‐R )‐2‐azabicyclo‐[3.3.0]octane‐3‐carboxylic acid. The catalytic efficiency of the chiral 1,3,2‐oxazaphospholidine‐borane complexes 3a, 3b , and 8c was examined in the enantioselective borane reduction of some ketones.