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Highly stereospecific conversion of C-centrochirality of a 3,4-dihydro-2H-1,1′-binaphthalen-1-ol into axial chirality of a 3,4-dihydro-1,1′-binaphthalene

✍ Scribed by Tetsutaro Hattori; Masamitsu Date; Kenta Sakurai; Naoya Morohashi; Hiroshi Kosugi; Sotaro Miyano

Book ID
104231756
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
90 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

C-Centrochirality of 3,4-dihydro-2%-methoxy-2-methyl-2H-1,1%-binaphthalen-1-ol (R,R)-3e, which had been prepared by diastereoselective 1,2-addition of a 2-methoxy-1-naphthylytterbium reagent to 2-methyl-1-tetralone (R)-1b, was stereospecifically converted into axial chirality of 3,4-dihydro-2%-methoxy-2-methyl-1,1%-binaphthalene (aR)-4 with up to 95% ee by dehydration with trifluoroacetic anhydride. DDQ aromatization of (aR)-4 gave 2%-methoxy-2-methyl-1,1%-binaphthalene (aR)-5 without appreciable loss of the axial integrity. The net process provides a potential access to nonracemic 1,1%-binaphthalenes.

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