Asymmetric Synthesis of cis-5-tert-Butylproline with Metal Carbenoid NH Insertion
- 1 June 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (13) , 5147-5152
- https://doi.org/10.1021/jo030081s
Abstract
The highly stereoselective intramolecular metal carbenoid insertion reaction of sulfinimine-derived δ-amino α-diazoesters is used to prepare cis-5-tert-butylproline. A concerted or nearly concerted metal carbenoid N−H insertion reaction mechanism is proposed.Keywords
This publication has 17 references indexed in Scilit:
- Mechanism of C−H Bond Activation/C−C Bond Formation Reaction between Diazo Compound and Alkane Catalyzed by Dirhodium TetracarboxylateJournal of the American Chemical Society, 2002
- Rhodium-Mediated Intramolecular C−H Insertion: Probing the Geometry of the Transition StateThe Journal of Organic Chemistry, 1998
- Asymmetric Strecker Synthesis Using Enantiopure Sulfinimines and Diethylaluminum Cyanide: The Alcohol EffectThe Journal of Organic Chemistry, 1996
- 5-tert-ButylprolineThe Journal of Organic Chemistry, 1996
- Predicting the Diastereoselectivity of Rh-Mediated Intramolecular C−H InsertionJournal of the American Chemical Society, 1996
- Computer-Assisted Mechanistic Evaluation of Organic Reactions. 24. Carbene ChemistryThe Journal of Organic Chemistry, 1994
- Organic Synthesis with .alpha.-Diazo Carbonyl CompoundsChemical Reviews, 1994
- Electronic and steric control in carbon-hydrogen insertion reactions of diazoacetoacetates catalyzed by dirhodium(II) carboxylates and carboxamidesJournal of the American Chemical Society, 1993
- An improved method for the synthesis of .alpha.-diazo ketonesThe Journal of Organic Chemistry, 1990
- Catalytic methods for metal carbene transformationsChemical Reviews, 1986