Novel cyclic sugar imines: Carbohydrate mimics and easily elaborated scaffolds for aza-sugars

Organic Letters

Volumn 4, Issue 1, 2002, Pages 103-106

  Davis, Benjamin G ^a,c   Maughan, Michael A T ^c   Chapman, Timothy M ^a,c   Villard, Renaud ^c   Courtney, Steve ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b Oxford GlycoSciences   (United Kingdom)

^c DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; HETEROCYCLIC COMPOUND; IMINE;

ARTICLE; CYCLIZATION; MOLECULAR MIMICRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

AZA COMPOUNDS; CARBOHYDRATES; CYCLIZATION; IMINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR MIMICRY;

EID: 0037050415     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016970o     Document Type: Article

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39. Compound 23 is in fact a product of the novel addition reactions described below (see Table 1).
40. This range of imines allowed us to successfully demonstrate representative additions to both aldimines 10, 15, 18 and ketimines 11, 21. Additions to other aldimines 22, 26 and ketimine 25 are now underway.
41. Tentatively characterized as addition product of exocyclic enamine tautomer of 10 to 10 itself, which was catalyzed by Mg salts; the synthetic utility of this dimerization is currently being explored.
42. Other complementary methods exist for creating potentially electrohphilic azomethine carbons, e.g., nitrones or acyl immoniums, However, these require additional steps to both introduce and remove additional functionality.