Use of a New Spirophosphine To Achieve Catalytic Enantioselective [4 + 1] Annulations of Amines with Allenes To Generate Dihydropyrroles
- Creators
- Kramer, Søren
-
Fu, Gregory C.
Abstract
Due in part to the common occurrence of five-membered nitrogen heterocycles in bioactive molecules, the discovery of methods for the enantioselective synthesis of such structures is a useful endeavor. Building on a single example by Tong of a phosphine-catalyzed [4 + 1] annulation of an amine with an allene that furnished an achiral dihydropyrrole in 22% yield, we have developed, with the aid of a new chiral spirophosphine catalyst, a method with increased utility, specifically, improved yield, enhanced scope (the use of γ-substituted allenes), and good ee. The enantioenriched dihydropyrrole products can be transformed into other interesting families of compounds with very good stereoselectivity.
Additional Information
© 2015 American Chemical Society. Received: February 23, 2015. Publication Date (Web): March 17, 2015. This study is dedicated to Prof. Stephen L. Buchwald, a friend and a mentor, on the occasion of his 60th birthday. Support has been provided by the National Institutes of Health (National Institute of General Medical Sciences: R01-GM57034) and the Lundbeck Foundation (postdoctoral fellowship for S.K.). We thank Dr. Nathan D. Schley, Dr. Michael K. Takase (Caltech X-ray Crystallography Facility; a Bruker KAPPA APEX II X-ray diffractometer was purchased via NSF CRIF:MU award CHE-0639094 to Caltech), Dr. David G. VanderVelde (Caltech NMR Facility), Dr. Scott C. Virgil (Caltech Center for Catalysis and Chemical Synthesis, supported by the Gordon and Betty Moore Foundation), and Dr. Susan L. Zultanski (initial synthesis of phosphine 1) for assistance.Attached Files
Accepted Version - nihms687862.pdf
Supplemental Material - ja5b01944_si_001.pdf
Supplemental Material - ja5b01944_si_002.cif
Files
Additional details
- PMCID
- PMC4433051
- Eprint ID
- 55966
- Resolver ID
- CaltechAUTHORS:20150323-103746266
- NIH
- R01-GM57034
- Lundbeck Foundation
- NSF
- CHE-0639094
- Gordon and Betty Moore Foundation
- Created
-
2015-03-23Created from EPrint's datestamp field
- Updated
-
2022-06-14Created from EPrint's last_modified field