New chiral oxazaphospholidine oxides as highly efficient catalysts in the enantioselective reduction of ketones

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8351-8354

  Peper, Viola ^a   Martens, Jürgen ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; BENZYL ALCOHOL DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030580344     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01928-4     Document Type: Article

References (24)

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18. 3).-
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22. 11. The oxazaphospholidine oxide 5 was mentioned by Wills et al. (see footnote 6), but wasn't tested as catalyst in the enantioselective reduction of ketones by borane.
23. 12. Typical reduction procedure see: V. Peper, J. Martens, Chem. Ber. 1996, 129, 691. The enantiomeric excess was determined by GC analysis using a SGE Cydec-B as chiral column with n-hexane as eluant.
24. 13. Catalyst 4: 10 mol% (91%ee), 2 mol% (86%ee) and 1 mol% (77%ee). Catalyst 5: 10 mol% (>99%ee), 2 mol% (97%ee), 1 mol% (96%ee), 0.8 mol% (94%ee), 0.5 mol% (88%ee), 0.3 mol% (64%ee), 0.2 mol% (62%ee) and 0.1 mol% (61%ee). Reduction procedure: see footnote 12.