Abstract
An asymmetric Claisen rearrangement using Oppolzer's camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.
Original language | English |
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Pages (from-to) | 13330-13344 |
Number of pages | 15 |
Journal | Molecules |
Volume | 17 |
Issue number | 11 |
DOIs | |
Publication status | Published - 2012 Nov |
Keywords
- Camphorsultam
- Chiral auxiliary
- Claisen rearrangement
- Quaternary stereocenter
- Total synthesis
ASJC Scopus subject areas
- Analytical Chemistry
- Chemistry (miscellaneous)
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry