Asymmetric Synthesis of 2-Aryl-Tetrahydropyrans via Arene Chromium Tricarbonyl Methodology 1: cis-2-Aryl-4-Chloro-Tetrahydropyrans

DOI: 10.1016/S0957-4166(00)82002-9

Source and publish data:

Tetrahedron Asymmetry p. 1085 - 1088 (1991)

Update date:2022-08-03

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Authors:

Davies, Stephen G.

Donohoe, Timothy J.

Lister, M. Anne

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Article abstract of DOI:10.1016/S0957-4166(00)82002-9

Treatment of acetals derived from ortho substituted benzaldehyde chromium tricarbonyl complexes and methanol with homoallylic alcohol and titanium tetrachloride produces the corresponding (RS,RS,SR,RS)-cis-2-aryl-4-chloro-tetrahydropyran complexes completely diastereoselectively.Thus, by this method, homochiral (R)-(-)-o-anisaldehyde chromium tricarbonyl is converted, after decomplexation, to homochiral (R,S)-(+)-cis-2-o-anisyl-4-chloro-tetrahydropyran.

Full text of DOI:10.1016/S0957-4166(00)82002-9

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