Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- And diversity-oriented synthesis: New insights into glycal reactivity Journal Article

  

Authors:	Moilanen, S. B.; Tan, D. S.
Article Title:	Enantioselective synthesis of erythro-4-deoxyglycals as scaffolds for target- And diversity-oriented synthesis: New insights into glycal reactivity
Abstract:	An efficient, enantioselective synthesis of eryithro-4-deoxygtycals has been developed using asymmetric aldehyde allylation and tungsten-catalyzed alkynol endo-cycloisomerization as the key steps. These versatile synthetic scaffolds have been elaborated to a variety of products using stereoselective transformations that are complementary to those available using the corresponding threo glycals. This work has provided valuable insights into the relationships between glycal structure and reactivity. In addition, a new diene-forming side reaction during tungsten-catalyzed alkynol cycloisomerization has been discovered. © The Royal Society of Chemistry 2005.
Keywords:	chemistry; nuclear magnetic resonance spectroscopy; chemical structure; molecular structure; catalysis; cyclization; aldehydes; synthesis; synthesis (chemical); stereochemistry; stereoisomerism; photochemistry; isomerization; reduction; alkyne; alkynes; single heterocyclic rings; heterocyclic compounds, 1-ring; reaction kinetics; enantioselective synthesis; substitution reactions; cycloisomerization; glycal reactivity; glycal structures; ethylamine; triethylamine; tungsten derivative; ethylamines; tungsten compounds
Journal Title:	Organic & Biomolecular Chemistry
Volume:	3
Issue:	5
ISSN:	1477-0520
Publisher:	Royal Society of Chemistry
Date Published:	2005-03-07
Start Page:	798
End Page:	803
Language:	English
DOI:	10.1039/b417429a
PUBMED:	15731865
PROVIDER:	scopus
DOI/URL:	http://www.scopus.com/inward/record.url?eid=2-s2.0-15244347851&partnerID=40&md5=d910b1fd7903e432265b62e889ba3d93
Notes:	--- - "Cited By (since 1996): 22" - "Export Date: 24 October 2012" - "Source: Scopus"

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