1242077-66-2Relevant academic research and scientific papers
Catalytic asymmetric synthesis of the endo -6-Aryl-8-oxabicyclo[3.2.1]oct- 3-en-2-one natural product from ligusticum chuanxing via 1,3-dipolar cycloaddition of a formyl-derived carbonyl ylide using Rh2(S -TCPTTL)4
Shimada, Naoyuki,Hanari, Taiki,Kurosaki, Yasunobu,Takeda, Koji,Anada, Masahiro,Nambu, Hisanori,Shiro, Motoo,Hashimoto, Shunichi
, p. 6039 - 6042 (2010)
The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition of a cyclic formyl-carbonyl ylide. Using this catalytic process, an asymmetric synthesis of endo-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural product 1 from Ligusticum chuanxing Hort. has been achieved.
