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Substituent effects in the selective reductive opening of epoxides with borohydrides in the presence of β‐cyclodextrin
Author(s) -
Doussot Joël,
Guy Alain,
Siaugue JeanMichel,
Ferroud Clotilde,
Guières Annie Fal
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:7<541::aid-chir5>3.0.co;2-g
Subject(s) - chemistry , regioselectivity , substituent , stereoselectivity , reactivity (psychology) , cyclodextrin , ring (chemistry) , aqueous solution , stereochemistry , medicinal chemistry , organic chemistry , computational chemistry , catalysis , medicine , alternative medicine , pathology
The opening of ortho ‐substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring‐opening are reported. The results obtained are compared with previous studies and have allowed some factors governing the reactivity, the regio‐ and stereoselectivity of this reaction to be evaluated. Preferential orientations of the substrate included inside the cyclodextrin are proposed from these results. Chirality 11:541–545, 1999. © 1999 Wiley‐Liss, Inc.