A dihydroisoxazole-based route to 2,3,6-trideoxy-3-aminohexose derivatives

Wade, Peter A.; Rao, J. Appa; Bereznak, James F.; Yuan, C.-K.

doi:10.1016/s0040-4039(01)93830-4

Cited by 13 publications

(2 citation statements)

References 17 publications

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“…The three carbons referring to C-1-C-3 in acosamine derivative 289 lie hidden in the dihydroisoxazolyl ring 286 in Wade's unprecedented synthetic strategy (Scheme 56). 155,156 Thus, aldehyde 288 was prepared by the stereoselective reductive cleavage reaction of benzylidenated dihydroisoxazolyl diol 287. This protected diol was prepared from 3-nitro-4,5-dihydroisoxazole (286) via sequential propynylation, Lindlar reduction, catalytic dihydroxylation, and protection.…”

Section: Scheme 54mentioning

confidence: 99%

Concepts for the Total Synthesis of Deoxy Sugars

2001

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Section: Scheme 54mentioning

confidence: 99%

Concepts for the Total Synthesis of Deoxy Sugars

2001

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“…Lithium 1-propynyltrialkylborates, formed by addition of propynyllithium to trialkylboranes, react with Trimethylsilylmethyl Trifluoromethanesulfonate followed by protonolysis to give allylsilanes (eq 9). 13 Propynyllithium displaces the nitro group of 3-nitro-4,5-dihydroisoxazole to give a precursor for deoxy-3-aminohexoses, 14 and reacts with the hindered aromatic chlorophosphine to give the 3H-phosphaallene after rearrangement (eq 10), while the less basic propynylmagnesium bromide gives the tautomeric alkynyl-1Hphosphine. 15 N,N-Bis(trimethylsilyl) ynamines, synthetic equivalents for primary ynamines, have been prepared by addition of propynyllithium to the crystalline hindered hydroxylamine mesitylenesulfonate (eq 11).…”

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confidence: 99%

Propynyllithium

Greeves

2001

Encyclopedia of Reagents for Organic Synthesis

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Asymmetric Dihydroxylation of Alkenes

2005

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The oxidation of alkenes to vicinal diols using osmium tetroxide is one of the most selective and reliable transformations in organic synthesis. The reaction stereospecifically produces a cis‐1,2‐glycol and is tolerant of a wide array of functional groups. Methods have been developed to oxidize alkenes stoichiometrically, as well as in the presence of catalytic amounts of osmium tetroxide, when a suitable secondary oxidant is present. The latter process is particularly useful considering the expense and toxicity of osmium tetroxide. The utility of dihydroxylation in organic synthesis is enhanced by the facile transformations of the cis‐1,2‐diol products into other useful derivatives. Among the most versatile intermediates are the corresponding cyclic sulfates, which serve as reactive epoxide equivalents that can be used singly or doubly displaced with amine‐, oxygen‐, sulfur‐, or carbon‐based nucleophiles. The reaction of osmium tetroxide with alkenes is accelerated by several orders of magnitude in the presence of coordinating amine ligands such as triethylamine, quinuclidine, or diazobicyclooctane. The logical extension to asymmetric osmylation of alkenes in the presence of chiral amine bases spurred the study of asymmetric dihydroxylation. The breakthrough of catalytic turnover in the cinchona alkaloid‐osmium tetroxide system revolutionized the field of asymmetric dihydroxylation. Specialized ligands have been developed to provide position selectivity in the dihydroxylation of polyenes, efficient kinetic resolution of racemic substrates, and high levels of enantioselectivity for each of six alkene classes.

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A dihydroisoxazole-based route to 2,3,6-trideoxy-3-aminohexose derivatives

Cited by 13 publications

References 17 publications

Concepts for the Total Synthesis of Deoxy Sugars

Concepts for the Total Synthesis of Deoxy Sugars

Propynyllithium

Asymmetric Dihydroxylation of Alkenes

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