Asymmetric synthesis of chiral secondary alcohols
AssigneeBoulder Scientific Company
InventorJeffrey M. Sullivan
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Abstract
A process for producing (R)-2-hydroxy-6-haloalkane is disclosed. In the first step, a cyclic alkanol is photohalogenated. In the second step, the photohalogenation product is reacted with a chiral catalyst and dialkyl zinc to produce (R)-2-hydroxy-6-haloalkane.
Claims5
A process for synthesizing a chiral secondary alcohol which comprises photohalogenating a cyclic alkanol to produce haloaldehyde and thereafter reacting said haloaldehyde with a dialkyl zinc in the presence of a chirally active catalyst to produce said chiral secondary alcohol.
A process for producing (R)-2-hydroxy-6-halohexane which consists essentially of the steps:
- (i) photohalogenating cyclopentanol to produce halopentanal, and
- (ii) reaching said halopentanal with dimethyl zinc in the presence of (lR,2S-C-1-N,N-dibutylnorephedrine) to produce (R)-6-halo-2-hexanol.
A process for producing (R)-2-acetoxy-6-chlorohexane which comprises:
- (i) photochloronating cyclopentanol to produce chloropentanal,
- (ii) reaching said chloropentanal with dimethyl zinc in the presence of (1R,2S-C-1-N,N-dibutylnorephedrine) to produce (R)-6-chloro-2-hexanol,
- (iii) acetylating said (R)-6-chloro-2-hexanol to produce (R)-2-acetoxy-6-chlorohexane, and
- (iv) recovering said (R)-2-acetoxy-6-chlorohexane product.
A process for producing (R)-2-acetoxy-6-bromohexane which comprises:
- (i) photobrominating cyclopentanol to produce bromopentanal,
- (ii) reaching said bromopentanal with dimethyl zinc in the presence of (1R,2S-C-1-N,N-dibutylnorephedrine) to produce (R)-6-bromo-2-hexanol,
- (iii) acetylating said (R)-6-bromo-2-hexanol to produce (R)-2-acetoxy-6-bromohexane, and
- (iv) recovering said (R)-2-acetoxy-6-bromohexane product.
Dependencies are inferred from the claim text.