Rhodium-catalyzed highly enantio- and diastereoselective cotrimerization of alkenes and dialkyl acetylenedicarboxylates leading to furylcyclopropanes

Organic Letters

Volumn 10, Issue 13, 2008, Pages 2825-2828

  Shibata, Yu ^a   Noguchi, Keiichi ^a   Hirano, Masao ^a   Tanaka, Ken ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 59949104627     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800966f     Document Type: Article

References (30)

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28. Importantly, ee values of cyclohexadiene 4 are lower than those of furylcyclopropane 3 (Scheme 5). We anticipated that cyclohexadienes 4 generated through intermediate E possess the absolute configurations opposite to those generated through intermediates A and B. Sterically less demanding monoene 1a reacts with 2a to give (-)-4aa through intermediates A and B, which might result in the high ee value of (-)-4aa. On the other hand, sterically demanding monoene 1e reacts with 2a to give (-)-4ea through not only intermediates A and B but also intermediate E, which might result in the low ee value of (-)-4ea. In the reaction of sterically more demanding monoene 1k with 2a, intermediate E might be formed predominantly to give cyclohexadiene (+)-4ka as a sole product with high ee. The opposite optical rotations, (-)-4aa/(-)-4ea vs (+)-4ka, might be correlated with the opposite absolute configurations.
29. In this reaction, no conversion of 1k was observed using (R)-Segphos as a ligand.
30. Yamamoto, Y.; Kitahara, H.; Ogawa, R.; Kawaguchi, H.; Tatsumi, K.; Itoh, K. J. Am. Chem. Soc. 2000, 122, 4310.