Highly enantioselective reduction of 3,4-dihydro-2,2-dimethyl-2H- 1 -benzop
yran-4-ones 3 a-e by BH3 was achieved in the presence of catalytic amounts
of Corey's oxazaborolidine 4 to afford the corresponding 3,4-dihydro-2,2-di
methyl-2H-1-benzopyran-4-ols 2a-e in quantitative yields. These benzopyran-
4-ols 2a-e were converted into the chiral 4-amino-3,4-dihydro-2,2-dimethyl-
2H-1-benzopyran 1a-e by mesylation, followed by introduction of an azide gr
oup by tetra-n-butyl-ammonium azide, and finally by reduction of the azide
6 with triphenylphosphine under very mild conditions without loss of stereo
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