Abstract
An efficient asymmetric synthesis of 1,2,3-trisubstituted cyclopentanes and cyclohexanes is described. Three methods were developed for the preparation of the 2,3-disubstituted cyclopentenones and cyclohexenones, which are key achiral building blocks. These intermediates are reduced catalytically with (R)-2-methyloxazaborolidine in high yield (82-98%) and excellent ee (89-96%). Directed reduction of the chiral allylic alcohols using Red-Al gives exclusively the 1,2-anti stereochemistry (>99:1). Epimerization of the ester center followed by saponification/crystallization affords the desired hydroxyacids in good yield (65-70%) and in high enantiomeric excess (>99%).
Original language | English (US) |
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Pages (from-to) | 5993-6000 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 67 |
Issue number | 17 |
DOIs | |
State | Published - Aug 23 2002 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Organic Chemistry