Catalytic hydroformylation of (1S,5S)-(−)- and (1R,5R)-(+)-β-pinene: stereoselective synthesis and spectroscopic characterization of (1S,2R,5S)-, (1S,2S,5S)-, (1R,2R,5R)- and (1R,2S,5R)-10-formylpinane
✍ Scribed by Fabrizio Azzaroni; Paolo Biscarini; Silvia Bordoni; Giuliano Longoni; Emanuela Venturini
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- English
- Weight
- 820 KB
- Volume
- 508
- Category
- Article
- ISSN
- 0022-328X
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## Abstract Starting from 2,3‐__O__‐(3‐pentylidene)‐D‐glyceraldehyde (3), we prepared the bicyclic pheromone (1__S__,2__S__,4__R__,5__R__)‐(−)‐β‐multistriatin (1) on a gram scale. Key steps of the synthesis are a __cis__‐selective Wittig olefination followed by diastereo‐selective Michael addition
The condensation of (1 R,2S) or (lS,2S)-N,N'-dimethyI-l-phenylpropane-l 2-diamines with aldehydes gives respectively two diastereorneric 2-alkyl-l,3,4-trimethyI-S-phen limidazolidines. At thermodynamical equilibrium the major isomer in the erythro series is this one where t f ! e substituents at pos