INTRAMOLECULAR FORMAL [3- STEREOSELECTIVE SYNTHESIS OF 1,2,3,4,4A,9A-HEXAHYDROFLUORENES(2] CYCLOADDITION OF ALKENES AND BENZYLIC CATIONS )

Authors
ANGLE SR FRUTOS RP
Citation
Sr. Angle et Rp. Frutos, INTRAMOLECULAR FORMAL [3- STEREOSELECTIVE SYNTHESIS OF 1,2,3,4,4A,9A-HEXAHYDROFLUORENES(2] CYCLOADDITION OF ALKENES AND BENZYLIC CATIONS ), Journal of organic chemistry, 58(19), 1993, pp. 5135-5144
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
19
Year of publication
1993
Pages
5135 - 5144
Database
ISI
SICI code
0022-3263(1993)58:19<5135:IF[SSO>2.0.ZU;2-J
Abstract
The Lewis acid-promoted intramolecular formal [3 + 2]-atom 'cycloaddit ion' of alkenes with benzylic cations derived from benzylic alcohols a nd quinone methides affords products in good yield and with remarkable stereoselectivity. Benzylic alcohol 20 affords hexahydrofluorene 36 w ith three new stereogenic centers in 73% yield as a 10:1 mixture of di astereomers. The scope and limitations of these reactions were explore d by varying the substitution pattern on the benzylic cation, the cycl ization initiators, and the alkene terminators.