Stereoselective Synthesis of Pyrrolidines from N-Allyl Oxazolidines via Hydrozirconation−Cyclization
- 1 October 2005
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (22), 4887-4889
- https://doi.org/10.1021/ol0517776
Abstract
[reaction: see text] A new diastereoselective synthesis of pyrrolidines from readily available chiral N-allyl oxazolidines is presented. The construction of the pyrrolidine ring is achieved via a tandem hydrozirconation-stereoselective Lewis acid mediated cyclization sequence.Keywords
This publication has 16 references indexed in Scilit:
- Intramolecular Hydroamination of Unactived Olefins with Ti(NMe2)4 as a PrecatalystOrganic Letters, 2005
- Hammett Correlation of Nornicotine Analogues in the Aqueous Aldol Reaction: Implications for Green OrganocatalysisThe Journal of Organic Chemistry, 2005
- Conjugate Additions of Nitroalkanes to Electron-Poor Alkenes: Recent ResultsChemical Reviews, 2005
- Stereoselective synthesis of substituted N-heterocycles via sequential cross metathesis—reductive cyclizationTetrahedron Letters, 2005
- Asymmetric Synthesis of 3-Substituted Proline Chimeras Bearing Polar Side Chains of Proteinogenic Amino AcidsThe Journal of Organic Chemistry, 2004
- Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majusculaElectronic supplementary information (ESI) available: 1H NMR spectrum of synthetic (+)-kalkitoxin in C6D6. See http://www.rsc.org/suppdata/ob/b4/b404205k/Organic & Biomolecular Chemistry, 2004
- Catalytic, Three-Component Assembly Reaction for the Synthesis of PyrrolidinesOrganic Letters, 2003
- Kinetic and Stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of Proline-Catalyzed Intra- and Intermolecular Aldol ReactionsJournal of the American Chemical Society, 2002
- Synthesis of 2,5-disubstituted pyrrolidinesTetrahedron: Asymmetry, 1996
- C2 symmetry and asymmetric inductionChemical Reviews, 1989