Design and Synthesis of the First Spiro Bis(isoxazoline) Derivatives as Asymmetric Ligands

Organic Letters - Tập 1 Số 11 - Trang 1795-1797 - 1999
Midori A. Arai1, Takayoshi Arai1, Hiroaki Sasai1
1The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan

Tóm tắt

Từ khóa


Tài liệu tham khảo

(a) Sainsbury, M.Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.  Pergamon Press:  Oxford, 1991; Vol. 8, pp 646−648.

(b) Curran, D. P.Advances in Cycloaddition; Curran, D. P., Ed.  JAI Press:  Greenwich, CT, 1988; Vol. 1, pp 129−189.

(c) Padwa, A.; Schoffstall, A. M.Advances inCycloaddition; Curran, D. P., Ed.  JAI Press:  Greenwich, CT, 1988; Vol. 2, pp 28−46.

Kozikowski A. P., 1984, Acc. Chem. Res., 17, 416, 10.1021/ar00108a001

Acidic, 1979, Bull. Chem. Soc. Jpn., 52, 587

Example, 1990, J. Org. Chem., 55, 3056, 10.1021/jo00297a020

Ab, 1995, Revision D.4

Review of the chiral bis(oxazoline) ligands:  Ghosh, A. K.; Mathivanan, P.; Cappiello, J.Tetrahedron:  Asymmetry1998,9, 1−45.

Recent, 1992, J. Chem. Soc., Chem. Commun., 493, 494

Bien S., 1974, J. Org. Chem., 39, 2260, 10.1021/jo00929a028

All calculations were performed using the teXsan crystallographic software package of Molecular Structure Corporation, b = 10.154(2) Å, c = 10.865(3) Å

HPLC conditions: 4 (EtOH 3.0 mL/min, 21 min, 29 min)

Enantiomeric excess was determined by13C NMR spectroscopy after derivatization with 1,2-diphenylethylenediamine. Alexakis, A.; Frutos, J. C.; Mangeney, P.Tetrahedron:  Asymmetry1993,4, 2431−2434.

Crystal, 2023, monoclinic