Addition of Bu3SnLi to tert-Butanesulfinimines as an Efficient Route to Chiral, Nonracemic α-Aminoorganostannanes
- 1 October 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (22) , 4215-4218
- https://doi.org/10.1021/ol035702i
Abstract
Addition of Bu3SnLi to tert-butanesulfinimines proceeds with high diastereoselectivities to provide the expected adducts in excellent yields and typically with dr = >99:1. These adducts are readily converted to enantiomerically enriched N-Boc-protected α-aminoorganostannanes with complete retention of configuration.Keywords
This publication has 18 references indexed in Scilit:
- Resolution of α-hydroxystannanes via norephedrine carbamatesTetrahedron, 2002
- A Relative Organolithium Stability Scale Derived from Tin−Lithium Exchange Equilibria. Substituent Effects on the Stability of α-Oxy- and α-Aminoorganolithium CompoundsJournal of the American Chemical Society, 2002
- A Theoretical Investigation into the Inversion Barrier of Dipole-Stabilized α-AminoorganolithiumsOrganic Letters, 2002
- Asymmetric Synthesis of syn- and anti-1,3-Amino AlcoholsJournal of the American Chemical Society, 2002
- Chemistry of N-Boc-N-tert-butylthiomethyl-Protected α-Aminoorganostannanes: Diastereoselective Synthesis of Primary β-Amino Alcohols from α-AminoorganostannanesThe Journal of Organic Chemistry, 2002
- Kinetics and Mechanism of the (−)-Sparteine-Mediated Deprotonation of (E)-N-Boc-N-(p-methoxyphenyl)-3-cyclohexylallylamineJournal of the American Chemical Society, 2001
- A facile three-step synthesis of 1,2-amino alcohols using the Ellman homochiral tert-butylsulfinamideTetrahedron Letters, 2001
- Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl iminesTetrahedron, 1999
- Asymmetric Synthesis of α,α-Dibranched Amines by the Trimethylaluminum-Mediated 1,2-Addition of Organolithiums to tert-Butanesulfinyl KetiminesJournal of the American Chemical Society, 1998
- Complex Induced Proximity Effects: Enantioselective Syntheses Based on Asymmetric Deprotonations of N-Boc-pyrrolidinesJournal of the American Chemical Society, 1994