Enantioselective Synthesis of 3-Methyleneindan-1-ols via a One-Pot Allylboration-Heck Reaction of 2-Bromobenzaldehydes

Organic Letters

Volumn 17, Issue 10, 2015, Pages 2514-2517

  Calder, Ewen D D ^a   Sutherland, Andrew ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

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EID: 84929590405     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b01047     Document Type: Article

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39. For example, reaction of 1b with (R)-TRIP-PA 7b at -50 C gave (R)-4b in 96% yield and 90:10 er. At -80 C, (R)-4b was isolated in 59% yield and 80:20 er.
40. The one-pot asymmetric process was not attempted using aryl bromides 1d and 1i as these compounds were found be insoluble in toluene at -50 C.
41. The assignment of the absolute configuration of 3-methyleneindan-1-ols prepared in this study was based on comparison of optical rotations and HPLC data of known compounds (see refs 4d, 5b, and 6).