Highly diastereoselective formation of 3,7-dioxabicyclo[3.3.0]octan-2-ones in reaction of 2-arylcyclopropanedicarboxylates with aromatic aldehydes using 1,2-zwitterionic reactivity type

Highly diastereoselective formation of 3,7-dioxabicyclo[3.3.0]octan-2-ones in reaction of 2-arylcyclopropanedicarboxylates with aromatic aldehydes using 1,2-zwitterionic reactivity type Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Output data

Year: 2017, Volume: 58, Number: 38, Pages: 3712-3716 Pages count : 5 DOI: 10.1016/j.tetlet.2017.08.025

Authors

Borisov Denis D. ¹ , Novikov Roman A. ¹ , Tomilov Yury V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russian Federation

A new reaction of 2-arylcyclopropane-1,1-dicarboxylates (ACDC) with aromatic aldehydes that occurs via generation of a 1,2-zwitterionic intermediate in the presence of GaCl3 has been developed. This process results in the 3,7-dioxabicyclo[3.3.0]octane frame by addition of two aldehyde molecules to an ACDC molecule. The reaction is a complex anionic-cationic cascade process involving the formation of two C–C bonds, two C–O bonds, and five stereocenters. The process occurs with high diastereoselectivity to give only one diastereomer. A probable reaction mechanism is suggested and confirmed by NMR monitoring data.

Borisov D.D. , Novikov R.A. , Tomilov Y.V.
Highly diastereoselective formation of 3,7-dioxabicyclo[3.3.0]octan-2-ones in reaction of 2-arylcyclopropanedicarboxylates with aromatic aldehydes using 1,2-zwitterionic reactivity type
Tetrahedron Letters. 2017. V.58. N38. P.3712-3716. DOI: 10.1016/j.tetlet.2017.08.025 WOS Scopus OpenAlex

≡ Web of science:	WOS:000411420800007
≡ Scopus:	2-s2.0-85027556103
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