New Aniline-Containing Amino Alcohols from trans-(R,R)-2-(2-Nitrophenyl)-3-phenyloxirane as Useful Intermediates for the Synthesis of Chiral Ligands, Bases, and Benzoxazine Nucleus

New enantiopure aniline-containing amino alcohols are directly derived from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane, by alternative regioselective double reductions. Subsequent selective alkylation procedures and derivatizations provide a rapid and high-yielding access to different chiral liga...

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Veröffentlicht in:	Journal of organic chemistry 2006-12, Vol.71 (26), p.9891-9894
Hauptverfasser:	Solladié-Cavallo, Arlette, Lupattelli, Paolo, Bonini, Carlo, Ostuni, Valeria, Di Blasio, Nadia
Format:	Artikel
Sprache:	eng
Schlagworte:	Amino Alcohols - chemical synthesis Amino Alcohols - chemistry Aniline Compounds - chemistry Benzoxazines - chemical synthesis Benzoxazines - chemistry Chemistry Epoxy Compounds - chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Ligands Molecular Conformation Noncondensed benzenic compounds Organic chemistry Preparations and properties Stereoisomerism Stilbenes - chemistry
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Beschreibung
Zusammenfassung:	New enantiopure aniline-containing amino alcohols are directly derived from trans-(R,R)-2-(2-nitrophenyl)-3-phenyloxirane, by alternative regioselective double reductions. Subsequent selective alkylation procedures and derivatizations provide a rapid and high-yielding access to different chiral ligands, bases, and benzoxazines, without loss of optical purity.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo0617969