Rhodium-Catalyzed Asymmetric [2 + 2 + 2] Cycloaddition of 1,6-Enynes with Cyclopropylideneacetamides

• Published in: Organic letters Vol. 18; no. 3; pp. 388 - 391
• Main Authors: Yoshizaki, Soichi, Nakamura, Yu, Masutomi, Koji, Yoshida, Tomoka, Noguchi, Keiichi, Shibata, Yu, Tanaka, Ken
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.02.2016; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; ALKENES; 4+2 CARBOCYCLIZATION; ETHYL CYCLOPROPYLIDENEACETATE; 3+2+2 COCYCLIZATION; COMPLEXES; REGIO; 2 DIFFERENT ALKYNES; CYCLOTRIMERIZATION; DIRECT INTERMOLECULAR HYDROACYLATION; ENANTIOSELECTIVE CONSTRUCTION

It has been established that a cationic rhodium­(I)/H8–BINAP complex catalyzes the asymmetric [2 + 2 + 2] cycloaddition of 1,6-enynes with cyclopropylideneacetamides to produce spirocyclohexenes in excellent enantioselectivity with retaining cyclopropane rings.