Palladium(0)-Mediated Preparation of trans-4-Substituted-1-(phthalimido)-2-cyclopentenes [1]

Abstract

The series of title compounds were found to be conven­iently available from the corresponding trans-4-chloro-1-(phthalimido)-2-cyclopentene. The allylic chlorocycloalkene was found to be an excellent substrate for Pd(0)-mediated acyloxylation with the salts of carboxylic acids. Using the allylic chlorocycloalkene as a coupling partner, the Pd(0)-mediated alkylation with active methylene compounds was facilitated in variable yields by promotion with organic bases such as DBU and 1,1,3,3-tetramethylguanidine. Using the Pd(0)-mediated protocol, the product 4-substituted-trans-1-phthalimido-2-cyclopentenes were obtained in modest to excellent yields overall.

Key words

alkylation - coupling reactions - cyclopentenes - imides - palladium

1

Presented at the 221^st National Meeting of the American Chemical Society, April 1-4, 2001, San Diego, California; ORGN 406.

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1

Presented at the 221^st National Meeting of the American Chemical Society, April 1-4, 2001, San Diego, California; ORGN 406.

18

For employment of the analogous phenylsulfonylnitro-methane in palladium-mediated alkylations, see ref. 5a

20

Carbon signals marked with an asterisk (*) represent methyl and methyne carbons as determined by APT experiments.

21

Prepared from (+)-8 which was derived (Method B) from the (+)-1R, 4S-phthalimido-2-cyclopentenol prepared by method of Deardorff (ref. [14a] ).