Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols

Barlow, J. J.; Block, Michael H.; Hudson, Julian A.; Leach, Alison; Longridge, J. L.; Main, Brian G.; Nicholson, Stuart

doi:10.1021/jo00045a030

J. Org. Chem.

1992

DOI: 10.1021/jo00045a030

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Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols

J. J. Barlow¹,

Michael H. Block²,

Julian A. Hudson³

et al.

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1992

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Cited by 10 publications

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“…Attempts to deprotect enantiomerically pure ketal (77) in acid lead to racemization. 86 The problem was traced to a pseudo-Smiles rearrangement of diol (78) shown in Scheme 8, activated by Nprotonation of the heterocycle. This had implications for the correct choice of deprotection conditions; brief exposure of the ketal to strong acid allowed deprotec-10 Probes of Polar Reactions Bentley and Jones88 have described new rate-product correlations for reactions in binary solvent mixtures involving general-base catalysis.…”

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confidence: 99%

Chapter 4. Reaction mechanisms. Part (ii) Polar reactions

Percy¹

1992

Annu. Rep. Prog. Chem., Sect. B

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The whole 1992 volume of Advances in Physical Organic Chemistry will interest readers of this chapter. Reviews by Williams,'" Lee,'b Bernasconi," and Ta-Shma and Rappoport I d covered, respectively, the relationship between effective charge and transition-state structure, the use of cross interaction coefficients in the diagnosis of reaction mechanisms, the principle of non-perfect synchronization, and solventinduced changes in the selectivity of solvolysis reactions. The first issue of Accounts of Chemical Research contained a number of relevant articles: one described Bunnett's work on the dehalogenation of aryl halides by SET processes;2 mechanisms of amide hydrolysis in aqueous media were also d i s c ~s s e d . ~Elsewhere, the conceptual basis of face-selectivity in carbonyl-group addition reactions was a p p r a i ~e d , ~ and aspects of aromatic chemistry were reviewed including the electrophilic substitution reactions of heterocyclic compoundsS and vicarious nucleophilic substitutions.6The roles of ion-pair exchange processes and their manifestation in salt effects were reviewed,' and scales of solvent ionizing power based upon the solvolyses of benzylic substrates were surveyed.8 A number of aspects of nucleophilic aliphatic substitution were summarized and discussed, including the intervention of single electron transfer (SET) processes' and theoretical aspects of the S,2 reaction."Other topics which received attention included mechanisms for the formation of ozonides," and the use of the endocyclic restriction test for the elucidation of transition-state geometries.' A set of guidelines for the publication of results in (a) A.

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confidence: 99%

Chapter 4. Reaction mechanisms. Part (ii) Polar reactions

Percy¹

1992

Annu. Rep. Prog. Chem., Sect. B

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Synthesis of optically active β,γ-alkynylglycine derivatives

Meffre¹,

Gauzy²,

Branquet³

et al. 1996

Tetrahedron

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Diols as substrates in lipase-catalyzed enantioselective acylations - a brief review

Theil

1994

Catalysis Today

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Acid catalyzed racemization of 1-(heterocyclyloxy)-2,3-propanediols

Cited by 10 publications

References 0 publications

Chapter 4. Reaction mechanisms. Part (ii) Polar reactions

Chapter 4. Reaction mechanisms. Part (ii) Polar reactions

Synthesis of optically active β,γ-alkynylglycine derivatives

Diols as substrates in lipase-catalyzed enantioselective acylations - a brief review

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