Stereospecific and Stereoselective Rhodium(I)-Catalyzed Intramolecular [2+2+2] Cycloaddition of Allene-Ene-Ynes: Construction of Bicyclo[4.1.0]heptenes

• Published in: Angewandte Chemie International Edition Vol. 54; no. 4; pp. 1240 - 1244
• Main Authors: Ohta, Yuu, Yasuda, Shigeo, Yokogawa, Yuka, Kurokawa, Kei, Mukai, Chisato
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 19.01.2015; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: alkynes; Alkynes - chemistry; allenes; Bridged Bicyclo Compounds - chemistry; Catalysis; Chemistry; Chemistry, Multidisciplinary; Construction; Cycloaddition; Cycloaddition Reaction; cycloadditions; Cyclopropane; Cyclopropanes - chemistry; Derivatives; diastereoselectivity; Physical Sciences; rhodium; Rhodium - chemistry; Science & Technology; Stereoisomerism; allenes; ENTRY; alkynes; DIELS-ALDER REACTION; COMPLEXES; CYCLOISOMERIZATION; cycloadditions; BOND ACTIVATION; diastereoselectivity; SKELETONS; CYCLIZATION; rhodium
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201409155

Treatment of the allene‐ene‐yne substrates with [{RhCl(CO)2}2] effected the intramolecular [2+2+2]‐type ring‐closing reaction to produce various of tri‐ and tetracyclic derivatives containing a cyclopropane ring. The reaction is highly stereoselective as well as stereospecific with good to excellent yields. Two by three: Treatment of allene‐ene‐yne substrates with [{RhCl(CO)2}2] effected the intramolecular [2+2+2]‐type ring‐closing reaction to produce various of tri‐ and tetracyclic derivatives containing a cyclopropane ring. The reaction is highly stereoselective as well as stereospecific with good to excellent yields.