Enantioselective alkylative double ring opening of epoxides: Synthesis of enantioenriched unsaturated diols and amino alcohols

Angewandte Chemie - International Edition

Volumn 41, Issue 22, 2002, Pages 4313-4316

  Hodgson, David M ^a   Maxwell, Christopher R ^a   Miles, Timothy J ^a   Paruch, Edyta ^a   Stent, Matthew A H ^a   Matthews, Ian R ^b   Wilson, Francis X ^c   Witherington, Jason ^d  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

^c ROCHE PRODUCTS LTD   (United Kingdom)

^d Glaxo Smith Kline   (United Kingdom)

Author keywords

Alkenes; Amino alcohols; Diols; Enantioselectivity; Epoxides

Indexed keywords

ALCOHOLS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHIRAL LIGANDS;

AROMATIC COMPOUNDS;

ALKENE DERIVATIVE; AMINOALCOHOL; CARBENOID; EPOXIDE; FURAN DERIVATIVE; LIGAND; LITHIUM; ORGANOLITHIUM COMPOUND; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037112715     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021115)41:22<4313::AID-ANIE4313>3.0.CO;2-B     Document Type: Article

References (32)

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20. The epoxides in Table 1 are known (entries 1 and 2: P. L. Barili, G. Berti, E. Mastrorilli, Tetrahedron 1993, 49, 6263-6276; entries 8 and 9: L. G. French, T. P. Charlton, Heterocycles 1993, 35, 305-313; entry 10: L. G. French, E. E. Fenlon, T. P. Charlton, Tetrahedron Lett. 1991, 32, 851-854), prepared from the known alkenes (entries 4-7: M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979), or derived from 8-oxabicyclo[3.2.1]oct-6-en-3-one (entries 11-13: H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201).
21. The epoxides in Table 1 are known (entries 1 and 2: P. L. Barili, G. Berti, E. Mastrorilli, Tetrahedron 1993, 49, 6263-6276; entries 8 and 9: L. G. French, T. P. Charlton, Heterocycles 1993, 35, 305-313; entry 10: L. G. French, E. E. Fenlon, T. P. Charlton, Tetrahedron Lett. 1991, 32, 851-854), prepared from the known alkenes (entries 4-7: M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979), or derived from 8-oxabicyclo[3.2.1]oct-6-en-3-one (entries 11-13: H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201).
22. The epoxides in Table 1 are known (entries 1 and 2: P. L. Barili, G. Berti, E. Mastrorilli, Tetrahedron 1993, 49, 6263-6276; entries 8 and 9: L. G. French, T. P. Charlton, Heterocycles 1993, 35, 305-313; entry 10: L. G. French, E. E. Fenlon, T. P. Charlton, Tetrahedron Lett. 1991, 32, 851-854), prepared from the known alkenes (entries 4-7: M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979), or derived from 8-oxabicyclo[3.2.1]oct-6-en-3-one (entries 11-13: H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201).
23. The epoxides in Table 1 are known (entries 1 and 2: P. L. Barili, G. Berti, E. Mastrorilli, Tetrahedron 1993, 49, 6263-6276; entries 8 and 9: L. G. French, T. P. Charlton, Heterocycles 1993, 35, 305-313; entry 10: L. G. French, E. E. Fenlon, T. P. Charlton, Tetrahedron Lett. 1991, 32, 851-854), prepared from the known alkenes (entries 4-7: M. Nakamura, A. Hirai, E. Nakamura, J. Am. Chem. Soc. 2000, 122, 978-979), or derived from 8-oxabicyclo[3.2.1]oct-6-en-3-one (entries 11-13: H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201).
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