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Diastereoselective [3+2]-photocycloaddition of chiral 1,4-naphthalenedicarboxylic esters to alkenes

✍ Scribed by Yasuo Kubo; Masahiro Yoshioka; Satoshi Nakajima; Isamu Inamura

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 216 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00180-x

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✦ Synopsis

3+2]-Photocycloaddition of di-(-)-menthyl, di-(-)-8-phenylmenthyl, and di-(-)-bornyl 1,4naphthalenedicarboxylates to alkenes, such as isobutene, styrene, and ~-methylstyrene, proceeded with diastereoselectivity, up to 62% diastereomeric excess (de), largely depending on the concavity of the auxiliary, steric bulk of the substituents of the alkenes, and reaction temperature. The de values remarkably increased with decrease of the reaction temperature, and linear dependence of ln(diastereomeric ratio) on lfI" was observed.

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