β,γ,-Unsaturated α-amino acid δ-lactones; precursors for polyhydroxy amino acids

Campbell, Malcolm M.; Floyd, A; Lewis, Terry W.; Mahon, Mary F.; Ogilvie, R. J.

doi:10.1016/s0040-4039(00)99633-3

Cited by 13 publications

(2 citation statements)

References 10 publications

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“…The Overman rearrangement has also been applied to many other substrates and some examples are given in the references. − An elegant application of this reaction has been published by Danishefsky et al for the synthesis of (±)-pancratistatin 23 (Scheme ) …”

Section: 1 Amination Of Allyl Alcohols (Mitsunobu Reaction Etc)mentioning

confidence: 99%

Allylic Amination

1998

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Section: 1 Amination Of Allyl Alcohols (Mitsunobu Reaction Etc)mentioning

confidence: 99%

Allylic Amination

1998

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“…Irradiation of the H-l multiplet (CH = CHa) in 11 resulted in collapse of the H-2 signal to a broad singlet, indicating 3</2,3 was less than ca. 2 Hz.…”

Section: Resultsmentioning

confidence: 99%

A study of the 3,3-sigmatropic rearrangement of chiral trichloroacetamidic esters

Doherty¹,

Kornberg²,

Reily³

1993

J. Org. Chem.

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TheMitsunobu Reaction

1992

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Alkyl and aryl phosphites and phosphines react with compounds having weak heteroatom–heteroatom bonds, such as SS, OO, etc., and with azo compounds to form reactive phosphonium salts. These phosphonium salts in turn promote “redox” condensation reactions with compounds having active hydrogens. The condensation reaction of alcohols using the redox couple of a triaryl‐ or trialkylphosphine and a dialkyl azodicarboxylate has become known as the Mitsunobu reaction, based on his pioneering work in the late 1960s. The overall reaction is summarized, wherein the alcohol (R 1 OH) and acidic compound (H–Nu) are condensed to form product (R 1 –Nu), while triphenylphosphine is oxidized to triphenylphosphine oxide and the azodicarboxylate is reduced to the hydrazine. Although the typical redox combination is diethyl azodicarboxylate (DEAD) and triphenylphosphine, many other combinations have found selected use. The reaction is generally limited to primary and secondary alcohols, although tertiary alcohols react in a few intramolecular and intermolecular reactions. For secondary alcohols the reaction usually proceeds with clean inversion of stereochemistry. The acidic component of the reaction generally has an aqueous p K a < 15, with intramolecular reactions providing the exceptions. Examples of H–Nu include oxygen nucleophiles such as carboxylic acids and phenols; nitrogen nucleophiles such as imides, hydroxamates, and heterocycles; sulfur nucleophiles such as thiols and thioamides; and carbon nucleophiles such as β‐ketoesters. Major reviews of the Mitsunobu reaction were published in 1981 by Mitsunobu and in 1983 by Castro. The former review concentrated on reactions using DEAD/triphenylphosphine, while the latter review focused on reactions in which halogens replaced the hydroxy group using reagents such as triphenylphosphine/carbon tetrachloride, triphenyl phosphite/iodomethane, and triphenylphosphine/ N ‐halosuccinimide. Reactions involving the DEAD/triphenylphosphine redox system are the principal subject of this chapter, with emphasis on the literature between 1981 and 1988.

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β,γ,-Unsaturated α-amino acid δ-lactones; precursors for polyhydroxy amino acids

Cited by 13 publications

References 10 publications

Allylic Amination

Allylic Amination

A study of the 3,3-sigmatropic rearrangement of chiral trichloroacetamidic esters

TheMitsunobu Reaction

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