B-[E-3-(diphenylamino)allyl]diisopinocampheylborane: an excellent reagent for the stereoselective synthesis of anti-β-diphenylamino alcohols
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 4,p. 339-341
- https://doi.org/10.1039/c39930000339
Abstract
anti-β-Amino alcohols have been produced with high relative and absolute stereochemical control in a simple one-pot process via the reaction of aldehydes with B-[(E)-3-(diphenylamino)allyl]diisopinocampheylborane and alkaline hydrogen peroxide work-up.Keywords
This publication has 13 references indexed in Scilit:
- Zirconium-mediated diastereoselective coupling reactions of chiral aldimine: Remarkable temperature-dependence of chiral inductionTetrahedron Letters, 1992
- Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactionsJournal of the American Chemical Society, 1992
- B-[3-((Diisopropylamino)dimethylsilyl)allyl]diisopinocampheylborane: an excellent reagent for the stereoselective synthesis of anti vicinal diolsThe Journal of Organic Chemistry, 1991
- Chiral synthesis via organoboranes. 27. Remarkably rapid and exceptionally enantioselective (approaching 100% ee) allylboration of representative aldehydes at -100.degree. under new, salt-free conditionsThe Journal of Organic Chemistry, 1991
- Chiral synthesis via organoboranes. 24. B-allylbis(2-isocaranyl)borane as a superior reagent for the asymmetric allylboration of aldehydesJournal of the American Chemical Society, 1990
- Dichloroisopropoxytitanium nitronates as reagents for stereoselective Henry reactionsThe Journal of Organic Chemistry, 1989
- Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranesJournal of the American Chemical Society, 1986
- Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excessThe Journal of Organic Chemistry, 1986
- l-2-Nitro-1,3-alkanediols by stereoselective addition of nitroethanol to aldehydes. On the asymmetric electrophilic addition to double bondsJournal of the American Chemical Society, 1985
- Diastereoselective Synthesis of Nitroaldol DerivativesHelvetica Chimica Acta, 1982