Diamine-Free Lithiation−Trapping of N-Boc Heterocycles using s-BuLi in THF
- 18 August 2010
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 12 (18), 4176-4179
- https://doi.org/10.1021/ol1017799
Abstract
A diamine-free protocol for the s-BuLi-mediated lithiation-trapping of N-Boc heterocycles has been developed. In the optimized procedure, lithiation is accomplished using s-BuLi in THF at -30 °C for only 5 or 10 min. Subsequent electrophilic trapping or transmetalation-Negishi coupling delivered a range of functionalized pyrrolidines, imidazolidines, and piperazines in 43-83% yield.Keywords
This publication has 30 references indexed in Scilit:
- Pd-Catalyzed Enantioselective Aerobic Oxidation of Secondary Alcohols: Applications to the Total Synthesis of AlkaloidsJournal of the American Chemical Society, 2008
- Catalytic asymmetric synthesis of the alkaloid (+)-myrtineOrganic & Biomolecular Chemistry, 2008
- Process Development of the Synthetic Route to R116301Organic Process Research & Development, 2007
- Synthesis and Pharmacological Evaluation of Novel Octahydro-1H-pyrido[1,2-a]pyrazine as μ-Opioid Receptor AntagonistsJournal of Medicinal Chemistry, 2006
- Synthesis of 2-substituted piperazines via direct α-lithiationTetrahedron Letters, 2005
- Asymmetric Deprotonation by BuLi/(−)-Sparteine: Convenient and Highly Enantioselective Syntheses of (S)-2-Aryl-Boc-PyrrolidinesJournal of the American Chemical Society, 1996
- (−)-Sparteine-Mediated α-Lithiation of N-Boc-N-(p-methoxyphenyl)benzylamine: Enantioselective Syntheses of (S) and (R) Mono- and Disubstituted N-Boc-benzylaminesJournal of the American Chemical Society, 1996
- Generation of Enantiomerically Enriched Lithium Indenides by Means of (–)‐Sparteine: Structure, Stereoselective Substitution, and Solvent EffectsAngewandte Chemie, 1995
- .alpha.-Lithioamine synthetic equivalents: syntheses of diastereoisomers from Boc derivatives of cyclic aminesThe Journal of Organic Chemistry, 1993
- α-Lithioamine synthetic equivalents from dipole-stabilized carbanions: The t-Boc group as an activator for α′-lithiation of carbamatesTetrahedron Letters, 1989