Highly Enantioenriched 2‐Azabenzonorbornenes from 7‐Azabenzonorbornadienes by Asymmetric Hydroboration—Oxidation and Tandem Deoxygenation—Rearrangement—Electrophile Trapping.

Abstract

Trapping. -Asymmetric hydroboration of substrates (I) gives the alcohols (II) with excellent enantioselectivity. The xanthate (III) derived from (IIa) undergoes an interesting deoxygenative rearrangement-electrophilic trapping to yield the 3-exo substituted 2-azanorbornenes (V). Xanthates (VII) and (IX) derived from (IIb) and (IIc), resp., afford indenes (VIII) and (X) under similar conditions. -(HODGSON*, D. M.; WINNING, L. H.; Synlett 2006, 15, 2476-2479; Chem. Res. Lab., Dep. Chem., Univ. Oxford, Oxford OX1 3TA, UK; Eng.) -Mais 05-116