Syntheses and Reactions of Optically Active α-Aminoallenylstannanes
- 12 December 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (1) , 105-111
- https://doi.org/10.1021/jo0302861
Abstract
Lithiation/stannylation of optically active N-propargyloxazolidinones produced optically active alpha-oxazolidinonylallenylstannanes. Reaction of these with aldehydes in the presence of BF3.OEt2 produced beta-hydroxypropargylamines with high syn diastereoselectivity and ee. These were converted to gamma-hydroxy-beta-amino acids by oxidative cleavage of the alkyne.Keywords
This publication has 16 references indexed in Scilit:
- Copper Reagents: A New and Efficient Solution for the Selective Addition of Metallated Propargylic Amines to AldehydesOrganic Letters, 2003
- Highly Diastereoselective Synthesis of Propargylic 1,2-anti-Diol Derivatives Using α-AlkoxypropargylstannanesOrganic Letters, 2001
- First Stereoselective Inverse Demand [4 + 2] Cycloaddition Reactions of Novel Chiral Allenamides with Heterodienes. Preparation of Highly Functionalized 2-Arylpyranyl HeterocyclesOrganic Letters, 1999
- Asymmetric Synthesis of Stannanes and Silanes via Reaction of Chiral Imidazolidinone Carbene Complexes with Group 14 HydridesOrganometallics, 1998
- Synthesis of alkoxy-substituted allenyl- and propargylstannane reagents from carbene complexesTetrahedron Letters, 1995
- Rapid synthesis of functionalized, alkoxy-substituted, allylstannanes from carbene complexesTetrahedron Letters, 1995
- 1,2-Asymmetric induction in the tin-hydrogen bond insertion reaction of aliphatic Fischer carbene complexesJournal of the American Chemical Society, 1992
- Mechanism of carbene insertion into Group 4 element hydrides via chromium carbene complexes. Part II. Organogermanium and organotin hydridesJ. Chem. Soc., Dalton Trans., 1976
- Mechanism of carbene insertion into hydrides of Group 4 via chromium carbene complexes. Part I. Organosilicon hydridesJ. Chem. Soc., Dalton Trans., 1976
- Übergangsmetall—carben-komplexe : XLIV. Einschiebung des methoxyphenylcarben-liganden in die silicium—wasserstoff-bindungJournal of Organometallic Chemistry, 1972