Synthesis of highly enantioenriched chiral alpha-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 BF(3).OEt(2). 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-beta-aminoalcohols were firmly established from NMR data and after determination of several radiocrystallographic structures. Mechanisms were proposed in order to rationalize the observed selectivities.
Coeffard
Vincent
V
Université de Nantes, CNRS, Chimie et Interdisciplinarité: Synthèse, Analyse, Modelisation (CEISAM), UMR CNRS 6230, UFR des Sciences et des Techniques, 2 rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
Le Grognec
Erwan
E
Beaudet
Isabelle
I
Evain
Michel
M
Quintard
Jean-Paul
JP
D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D009947:Organotin Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D011412:Propanolamines / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D014633:Valine / Q000031:analogs & derivatives / Q000737:chemistry
D004983:Ethanolamines; D009947:Organotin Compounds; D010080:Oxazoles; D011412:Propanolamines; C064210:oxazolidine; C040994:valinol; C005332:N-phenylethanolamine; C034448:2-aminopropanol; D014633:Valine; D009584:Nitrogen; D005998:Glycine