- Collection:
- Atlanta University and Clark Atlanta University Theses and Dissertations
- Title:
- Asymmetric reduction of prochiral ketone by optically active polymeric reagents, 1995
- Creator:
- Liu, Yun
- Date of Original:
- 1995-03-01
- Subject:
- Degrees, Academic
Dissertations, Academic - Location:
- United States, Georgia, Fulton County, Atlanta, 33.749, -84.38798
- Medium:
- theses
- Type:
- Text
- Format:
- application/pdf
- Description:
- Prochiral acetophenone has been asymmetrically reduced by a new polymeric reagent. This polymeric reagent was prepared by complexing optically active poly (diphenyl-2-pyridylmethyl methacrylate) (PD2PyMA) with BH3 The presence of the 2-pyridyl groups in poly (diphenyl-2-pyridylmethyl methacrylate) allows for the preparation of the optically active polymer / borane complexes. The polymer complexes were used to reduce prochiral acetophenone asymmetrically to phenethyl alcohol. The optically active helical PD2?yMA was synthesized by living anionic polymerization techniques. The initiator for polymerization was prepared by complexing a chiral ligand with diphenylethylenediamine monolithium amide (DPEDA-Li). The optically active initiator was used to carry out the helix sense selective polymerization of PD2PyMA i.e. the resultant polymer is chiral because of the selective formation of one helix. The highest optical rotation of 1026 at 365 nm was obtained at room temperature. Acetophenone was reduced by the PD2PyMA/BH3 complex. The ketone was successfully asymmetrically reduced to give a chiral phenethyl alcohol. The (+)-Phenethyl alcohol was routinely obtained in about 60 % enantiomeric excess.
- External Identifiers:
- Metadata URL:
- http://hdl.handle.net/20.500.12322/cau.td:1995_liu_yun
- Rights Holder:
- Clark Atlanta University
- Holding Institution:
- Atlanta University Center Robert W. Woodruff Library
- Rights:
-
