Synthesis of the F-O-G fragment of ristocetin A via ruthenium-promoted intermolecular SNAr reaction

Pearson, Anthony J.; Velankar, Avdhoot; Heo, Jung-Nyoung

doi:10.3998/ark.5550190.0003.606

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Cited by 4 publications

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Sharpless Aminohydroxylation

2010

Comprehensive Organic Name Reactions and Reagents

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Several protocols have been reported for an osmium‐based enantiomeric transformation of olefins into corresponding α‐amino alcohols with nitrogen bound to a less‐substituted carbon using tert ‐alkyl imido osmium compound as the nitrogen source. Thus any of these procedures to give α‐amino alcohols are referred to as the sharpless aminohydroxylation. This reaction is sensitive towards the temperature and the geometry of olefinic substrate. Various nitrogen sources have been addressed for this reaction, such as chloramines‐T, N ‐chlorosodiocarbamates, and N ‐bromo‐ N ‐lithio salt of primary carboxamidesc and found that the protocol using N ‐chlorosodiocarbamates as the nitrogen source in the presence of silver nitrate offers better regioselectivity. This reaction is useful in organic synthesis for generating chiral vicinal amino alcohols with two functional groups.

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Sharpless Aminohydroxylation

2010

Comprehensive Organic Name Reactions and Reagents

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Diaryl Ether Formation in the Synthesis of Natural Products

2011

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The structural variety of naturally occurring diaryl ethers is illustrated and the various synthetic methods employed for the construction of diaryl ether linkages in related total syntheses are reviewed. Examples of successful applications of each method (including reaction conditions, diaryl ether substitution pattern, and, when appropriate, the size of the ring formed) are given in tabular format.

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