Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives

Authors
Cheung, E Netherton, MR Scheffer, JR Trotter, J Zenova, A
Citation
E. Cheung et al., Asymmetric induction through the use of remote covalent and ionic chiral auxiliaries in the solid state photochemistry of 2-benzoyladamantane-2-carboxylic acid derivatives, TETRAHEDR L, 41(49), 2000, pp. 9673-9677
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
49
Year of publication
2000
Pages
9673 - 9677
Database
ISI
SICI code
0040-4039(200012)41:49<9673:AITTUO>2.0.ZU;2-7
Abstract
Attachment of chiral auxiliaries to 2-benzoyladamantane-2-carboxylic acid, either covalently through ester formation with optically pure alcohols, or ionically via salt formation with optically pure amines, leads to substrate s whose irradiation in the crystalline state affords chiral rearranged phot oproducts in greater than or equal to 96% diastereo- and enantiomeric exces s. (C) 2000 Elsevier Science Ltd. All rights reserved.