Synthesis of Highly Enantioenriched Chiral α-Aminoorganotins via Diastereoselective Ring Opening of Chiral N-(Arenesulfonyl) 2-Tributylstannyloxazolidines

trans-N-(Arenesulfonyl)-2-tributylstannyloxazolidines derived from (R)-phenylglycinol were diastereoselectively ring-opened by soft organometallic reagents in the presence of BF3·OEt2. Both higher order organocuprates and allyltributyltin afforded the desired products in good-to-excellent yields and...

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Bibliographic Details
Published in:Journal of organic chemistry 2009-08, Vol.74 (16), p.5822-5838
Main Authors: Coeffard, Vincent, Le Grognec, Erwan, Beaudet, Isabelle, Evain, Michel, Quintard, Jean-Paul
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Condensed Matter
Ethanolamines
Exact sciences and technology
Glycine - analogs & derivatives
Glycine - chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Kinetics and mechanisms
Materials Science
Nitrogen - chemistry
Organic chemistry
Organotin Compounds - chemical synthesis
Organotin Compounds - chemistry
Oxazoles - chemistry
Physics
Preparations and properties
Propanolamines - chemistry
Reactivity and mechanisms
Stereoisomerism
Substrate Specificity
Valine - analogs & derivatives
Valine - chemistry
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Summary:trans-N-(Arenesulfonyl)-2-tributylstannyloxazolidines derived from (R)-phenylglycinol were diastereoselectively ring-opened by soft organometallic reagents in the presence of BF3·OEt2. Both higher order organocuprates and allyltributyltin afforded the desired products in good-to-excellent yields and high diastereoselectivities (dr up to 99/1). The stereochemical assignments of tributylstannyl-β-aminoalcohols were firmly established from NMR data and after determination of several radiocrystallographic structures. Mechanisms were proposed in order to rationalize the observed selectivities.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900223k