Journal article
Diastereo- and enantioselective hydride reductions of ketone phosphinyl imines to phosphinyl amines - Synthesis of protected amines and amino acids
Reductions in Organic Synthesis, v 641, pp 127-137
01 Jan 1996
Featured in Collection : UN Sustainable Development Goals @ Drexel
Abstract
Three protocols involving asymmetric reductions of ketone phosphinyl imines (1) to enantiomeric or diastereomeric phosphinyl amines (2), (which represent protected versions of primary amines), are presented, including the use of substrates containing diastereotopic faces to stereoselectively generate diastereomers, employment of chiral reagents for enantioselective reductions, and the utility of chiral auxiliary attachments for diastereoselective reductions followed by release of enantiomeric amines.
[GRAPHICS]
rded rate of borane coordination and competition from the endo transition state. Relative enantioselectivities were correctly predicted by ab initio calculations, and the calculated structures, energetics, and the existence of key intermediates were demonstrated to be sensitive to the level of theory applied. Ab initio calculations and utility of diphenyloxazaborolidine are described in detail.
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Details
- Title
- Diastereo- and enantioselective hydride reductions of ketone phosphinyl imines to phosphinyl amines - Synthesis of protected amines and amino acids
- Creators
- Robert O Hutchins - Drexel UniversityQi-Cong Zhu - Drexel UniversityJ AdamsS J Rao - Drexel UniversityE Oskay - Drexel UniversityA F AbdelMagid - Drexel UniversityMaryGail K Hutchins - Drexel University
- Contributors
- Ahmed F Abdel-Magid (Editor) - Drexel University
- Publication Details
- Reductions in Organic Synthesis, v 641, pp 127-137
- Series
- ACS Symposium Series; 641
- Publisher
- Amer Chemical Soc
- Number of pages
- 11
- Resource Type
- Journal article
- Language
- English
- Academic Unit
- Chemistry
- Web of Science ID
- WOS:A1996BG15J00008
- Other Identifier
- 991019170501104721
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- Web of Science research areas
- Chemistry, Multidisciplinary
- Chemistry, Organic