Synthesis of new enantiopure bicyclic 1,2-oxazines by addition of lithiated methoxyallene to chiral cyclic nitrones

European Journal of Organic Chemistry

Volumn , Issue 7, 2003, Pages 1153-1156

  Pulz, Robert ^a   Cicchi, Stefano ^b   Brandi, Alberto ^b   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Allenes; Cyclization; Heterocycles; Nucleophilic addition

Indexed keywords

1,2 OXAZINE DERIVATIVE; 3 (3 TERT BUTOXYPYRROLIDIN 2 YL) 3 METHOXYPROPAN 1 OL; 3 TERT BUTOXY 2 (1 METHOXYPROPA 1,2 DIENYL)PYRROLIDIN 1 OL; 3,4 BIS TERT BUTOXY 2 (1 METHOXYPROPA 1,2 DIENYL)PYRROLIDIN 1 OL; 5 TERT BUTOXY 4 METHOXY 4A,5,6,7 TETRAHYDRO 2H PYRROLIZIN N OXIDE; 5 TERT BUTOXY 4 METHOXY 4A,5,6,7 TETRAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE; 5,6 BIS TERT BUTOXY 4 METHOXY 3,4,4A,5,6,7 HEXAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZIN 3 OL; 5,6 BIS TERT BUTOXY 4 METHOXY 4A,5,6,7 TETRAHYDRO 2H PYRROLO[1,2 B][1,2]OXAZINE; ALLENE DERIVATIVE; AMINE OXIDE; HYDROXYL GROUP; NITRONE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CYCLIZATION; HYDROBORATION; HYDROGENATION; LITHIATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037394931     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390169     Document Type: Article

References (22)

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20. Reviews concerning reactions of lithiated alkoxyallenes: [12a] H.-U. Reißig, S. Hormuth, W. Schade, M. Okala Amombo, T. Watanabe, R. Pulz, A. Hausherr, R. Zimmer, Lectures in Heterocyclic Chemistry Vol XVI in J. Heterocycl. Chem. 2000, 37, 597-606. [12b] H.-U. Reißig, W. Schade, M. G. Okala Amombo, R. Pulz, A. Hausherr, Pure Appl. Chem. 2002, 74, 175-180. Reviews concerning reactions of nitrones with nucleophiles: [12c] P. Merino, S. Franco, F. L. Merchan, T. Tejero, Synlett 2000, 442-454. [12d] M. Lombardo, C. Trombini, Synthesis 2001, 759-774.
21. Reviews concerning reactions of lithiated alkoxyallenes: [12a] H.-U. Reißig, S. Hormuth, W. Schade, M. Okala Amombo, T. Watanabe, R. Pulz, A. Hausherr, R. Zimmer, Lectures in Heterocyclic Chemistry Vol XVI in J. Heterocycl. Chem. 2000, 37, 597-606. [12b] H.-U. Reißig, W. Schade, M. G. Okala Amombo, R. Pulz, A. Hausherr, Pure Appl. Chem. 2002, 74, 175-180. Reviews concerning reactions of nitrones with nucleophiles: [12c] P. Merino, S. Franco, F. L. Merchan, T. Tejero, Synlett 2000, 442-454. [12d] M. Lombardo, C. Trombini, Synthesis 2001, 759-774.
22. Reviews concerning reactions of lithiated alkoxyallenes: [12a] H.-U. Reißig, S. Hormuth, W. Schade, M. Okala Amombo, T. Watanabe, R. Pulz, A. Hausherr, R. Zimmer, Lectures in Heterocyclic Chemistry Vol XVI in J. Heterocycl. Chem. 2000, 37, 597-606. [12b] H.-U. Reißig, W. Schade, M. G. Okala Amombo, R. Pulz, A. Hausherr, Pure Appl. Chem. 2002, 74, 175-180. Reviews concerning reactions of nitrones with nucleophiles: [12c] P. Merino, S. Franco, F. L. Merchan, T. Tejero, Synlett 2000, 442-454. [12d] M. Lombardo, C. Trombini, Synthesis 2001, 759-774.