Chiral synthesis via organoboranes. 18. Selective reductions. 43. Diisopinocampheylchloroborane as an excellent chiral reducing reagent for the synthesis of halo …
M Srebnik, PV Ramachandran…
Index: Srebnik, Morris; Ramachandran, P.V.; Brown, Herbert C. Journal of Organic Chemistry, 1988 , vol. 53, # 13 p. 2916 - 2920
Full Text: HTML
Citation Number: 142
Abstract
Diisopinocampheylchloroborane, dIpc2BC1, reduces ring and chain substituted haloaralkyl ketones to the corresponding halo alcohols in excellent enantiomeric excess. In certain cases these alcohols can be upgraded by simple methods to essentially 100% ee. For instance,(+)-or (-)-3-chlorc-l-phenyl-l-propanol is initially obtained in 97% ee. Simple recrystallization then furnishes the pure enantiomers. These chiral halo alcohols are ...
Related Articles:
An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine
[Pandey, Rajesh Kumar; Fernandes, Rodney A.; Kumar, Pradeep Tetrahedron Letters, 2002 , vol. 43, # 25 p. 4425 - 4426]
A new chemoenzymatic enantioselective synthesis of R-(−)-tomoxetine,(R)-and (S)-fluoxetine.
[Kumar, Ashok; Ner, Dilip H.; Dike, Suneel Y. Tetrahedron Letters, 1991 , vol. 32, # 16 p. 1901 - 1904]
[Tetrahedron Letters, , vol. 43, # 31 p. 5435 - 5436]
Asymmetric hydrogenation of amino ketones using chiral RuCl2 (diphophine)(1, 2-diamine) complexes
[Journal of the American Chemical Society, , vol. 122, # 27 p. 6510 - 6511]
Asymmetric hydrogenation of amino ketones using chiral RuCl2 (diphophine)(1, 2-diamine) complexes
[Journal of the American Chemical Society, , vol. 122, # 27 p. 6510 - 6511]