Journal ArticleDOI
Regio- and Stereoselectivity of the Addition of O-, S-, N-, and C-Nucleophiles to the β Vinyl Oxirane Derived from d-Glucal
TLDR
6-O-Trityl- and 6-(O-benzyl)-substituted epoxide derived from D-glucal were examined in their addition reactions with O, C, N, and S-nucleophiles and a 1,2-syn-addition pathway was observed.Abstract:
6-O-Trityl- (1a) and 6-(O-benzyl)-substituted epoxide (1b) derived from d-glucal were examined in their addition reactions with O-, C-, N-, and S-nucleophiles. A 1,4-regio- and β-stereoselective or an anti 1,2-addition pathway is commonly observed depending on the ability of the nucleophile to coordinate with the oxirane oxygen. When TMSN3 or LiN3 are used as azide-based nucleophiles, a 1,2-syn-addition pathway is also observed.read more
Citations
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Recent Developments in the Ferrier Rearrangement
TL;DR: A review of recent developments in the use of promoters for the Ferrier rearrangement of O-, N-, C- and S-nucleophiles with glycals can be found in this paper.
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Chemical O-Glycosylations: An Overview
TL;DR: This Review will focus on the key developments towards chemical O‐glycosylations in the current century, including synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosidic bonds.
Journal ArticleDOI
Synthesis of syn and anti 1,4‐Diols by Copper‐Catalyzed Boration of Allylic Epoxides
TL;DR: In this paper, the regio-and diastereoselective Cu(I)-catalyzed boration of allylic epoxides offers a new approach for the diastore-selective synthesis of anti and syn 1,4-diols.
Journal ArticleDOI
Short, Enantioselective Total Syntheses of (−)‐8‐Demethoxyrunanine and (−)‐Cepharatines A, C, and D
TL;DR: All together!
References
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Journal ArticleDOI
Efficient preparation of intermediates corresponding to C22-C27 and C28-C34 of FK-506
TL;DR: In this paper, large-scale preparations of aldehyde 2 and sulfone 3 representing the C22-C27 and C28-C34 portions of the immunosuppressant FK-506 are described.
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New Stereoselective β-C-Glycosidation by Uncatalyzed 1,4-Addition of Organolithium Reagents to a Glycal-Derived Vinyl Oxirane
TL;DR: Reaction of epoxide 4 with a series of alkyl- and aryllithium reagents affords 2,3-unsaturated beta-C-glycosides with excellent 1,4-regioselectivity and complete stereoselectivities for the beta-glyCoside.
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Interpretation of conjugated oxiranes behavior toward nucleophiles
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A novel effective transition metal based salt-catalyzed azidolysis of 1,2-epoxides
TL;DR: In this paper, a simple, efficient, stereoselective, and in some cases usefully non-regiose-lective method for the synthesis of β-azido alcohols by the direct opening of 1,2-epoxides with 1,1,3,3-tetramethylguanidinium azide (TMGA) in CH3CN, catalyzed by simple transition metal-based salts, is described.
Journal ArticleDOI
New stereoselective beta-glycosylation via a vinyl oxirane derived from D-glucal.
TL;DR: The reaction of the vinyl oxirane 1 derived from d-glucal with a series of O-nucleophiles affords the corresponding 2-unsaturated β-O-glycosides in a completely stereoselective way (syn 1,4-addition pathway) as mentioned in this paper.