Asymmetric Reactions. III. Stereoselectivity Difference between Grignard and Alkyllithium Reactions with 2,3-O-Substituted-d-glyceraldehydes
- 1 October 1969
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 42 (10) , 2957-2961
- https://doi.org/10.1246/bcsj.42.2957
Abstract
Stereoselectivity has been investigated in addition reactions of 2,3-O-isopropylidene-d-glyceraldehyde (I) or 2,3-di-O-benzyl-d-glyceraldehyde (II) with phenylmagnesium bromide or phenyllithium. Stereoselectivity difference between the Grignard and phenyllithium reactions occurred in the case of compound (I): the phenyllithium reaction gives threo and the Grignard reaction erythro products predominantly. On the other hand, no difference in stereoselectivity has been observed between the reactions with 2,3-di-O-benzyl-d-glyceraldehyde (II): both reactions gave threo product predominantly.This publication has 9 references indexed in Scilit:
- Asymmetric Reactions. II. Anomalous Stereoselectivity of the Grignard Reaction with N-Benzyl-2,3-O-isopropylidene-d-glyceraldimineBulletin of the Chemical Society of Japan, 1969
- Steric Difference between the Substitution Reaction Products of Lithium Alkyls and Grignard Reagents with α-Aminonitriles.1 An Asymmetric ReproductionJournal of the American Chemical Society, 1964
- Configuration Assignments in Symmetrical Alkyl—Aryl Pinacols1The Journal of Organic Chemistry, 1963
- Synthesis of d-Threosamine and d-ErythrosamineBulletin of the Chemical Society of Japan, 1961
- Studies in Stereochemistry. XXIX. Neighboring Hydrogen Participation in Ionization to Give Ethylene Protonium Ions as Intermediates in the Wagner-Meerwein Rearrangement1Journal of the American Chemical Society, 1959
- Contact Electron-Spin Coupling of Nuclear Magnetic MomentsThe Journal of Chemical Physics, 1959
- The Stereochemical Configurations of the 1-C-Phenyl-D-pentitolsJournal of the American Chemical Society, 1951
- The Structures of Some Isopropylidene-aldehydo-L-arabinose DerivativesJournal of the American Chemical Society, 1948
- Synthesis of Some C-Substituted PentitolsJournal of the American Chemical Society, 1945