First transannular Diels–Alder reactions involving tetrasubstituted non-activated dienophiles-Reference-Cited by-同舟云学术

First transannular Diels–Alder reactions involving tetrasubstituted non-activated dienophiles

Published:1994-08-01 Issue:8 Volume:72 Page:1820-1829
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Roberge Jacques Y.,Giguere Pierre,Soucy Pierre,Dory Yves L.,Deslongchamps Pierre

Abstract

Transannular Diels–Alder reactions of four 14-membered macrocyclic trienes (27, 28, 43, and 44) possessing a dimethyl tetrasubstituted dienophile have been investigated. Macrocycles having a cis-trans-cis (CTC) (27), a CTT (43), and a TTT (44) geometry produced the predicted trans-syn-cis (TSC) (45), cis-anti-cis (CAC) (48), and TAC (49) tricycles, respectively. The TTC macrocycle (28) gave exclusively the TST tricycle (46), no CSC tricycle (47) being observed. TTT macrocycle (44) underwent macrocyclization at a lower temperature than the TTC isomer (28).

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v94-231

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