Published October 23, 2002
| Supplemental Material
Journal Article
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Non-Carbonyl-Stabilized Metallocarbenoids in Synthesis: The Development of a Tandem Rhodium-Catalyzed Bamford−Stevens/Thermal Aliphatic Claisen Rearrangement Sequence
- Creators
- May, Jeremy A.
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Stoltz, Brian M.
Chicago
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Abstract
A tandem rhodium-catalyzed Bamford−Stevens/Claisen rearrangement is presented. The tandem reaction uses Eschenmoser hydrazones for the in situ generation of non-carbonyl-stabilized diazo alkanes, which are presumably intercepted by Rh(II) catalysts to induce a 1,2-hydride migration. This sequence provides high levels of stereocontrol for the generation of simple acyclic (Z)-enol ethers. These enol ethers undergo either thermal or Lewis acid accelerated Claisen rearrangements to provide products of high diastereopurity. Also presented are cascade reactions, wherein a third chemical step occurs after the initial tandem sequence (i.e., Bamford−Stevens/Claisen/ene and Bamford−Stevens/Claisen/Cope).
Additional Information
© 2002 American Chemical Society. Received 5 August 2002. Published online 1 October 2002. Published in print 1 October 2002. The authors wish to thank the NSF (CHE-0135056), the Dreyfus Foundation, Merck Research Laboratories, and Abbott Laboratories for financial support.Attached Files
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Additional details
- Eprint ID
- 74338
- DOI
- 10.1021/ja028020j
- Resolver ID
- CaltechAUTHORS:20170215-150235551
- NSF
- CHE-0135056
- Camille and Henry Dreyfus Foundation
- Merck Research Laboratories
- Abbott Laboratories
- Created
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2017-02-15Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field