Topic
Mitsunobu reaction
About: Mitsunobu reaction is a research topic. Over the lifetime, 1887 publications have been published within this topic receiving 38990 citations.
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TL;DR: The diisopropyl azodicarboxylate-triphenylphosphine mediated cyclization of serine and allo-threonine derivatives provides peptide oxazolines, whereas cyclisation of threonine containing substrates leads to N-acyl aziridines.
122 citations
TL;DR: A catalytic Mitsunobu reaction system is described in which the azo reagent is use as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant.
Abstract: A catalytic Mitsunobu reaction system is described in which the azo reagent is used as an organocatalyst and iodosobenzene diacetate is used as the stoichiometric oxidant. In this system, iodosobenzene diacetate oxidizes the formed hydrazine byproduct to regenerate the azo reagent. Yields obtained in the catalytic reactions using a variety of carboxylic acids and alcohols were slightly lower than those obtained from corresponding stoichiometric reactions. Both primary and secondary alcohols can be used as substrates in this reaction system, with the secondary alcohols affording products with inverted stereochemistry at the carbinol center.
120 citations
TL;DR: In the presence of the diisopropyl azodicarboxylate/triphenylphosphine couple, alcohols react with zinc azide/bis-pyridine complex to give various azides via a Mitsunobu-type substitution as discussed by the authors.
Abstract: In the presence of the diisopropyl azodicarboxylate/triphenylphosphine couple, alcohols react with zinc azide/bis-pyridine complex to give various azides via a Mitsunobu-type substitution.
118 citations
TL;DR: This article classifies, compares, and contrasts various emerging strategies for product isolation in Mitsunobu reactions, a microcosm for the new field of strategy level separations.
Abstract: The Mitsunobu reaction is famous for its scope and power, but infamous for its separation headaches. Typically, the target product is enticed away from the reagent-derived byproducts by careful chromatography. The use of polymer-bound Mitsunobu reagents solves only half of the problem, because polymer-bound diethyl azodicarboxylate (DEAD) and phosphine reagents cannot be employed simultaneously. This article classifies, compares, and contrasts various emerging strategies for product isolation in Mitsunobu reactions. Because so many different strategies have been used, the Mitsunobu reaction is a microcosm for the new field of strategy level separations.
112 citations
TL;DR: In this article, Cinchonine and quinine were allowed to react with hydrazoic acid in a Mitsunobu reaction to yield the corresponding azides with inversion of configuration at C 9.
Abstract: Cinchonine and quinine were allowed to react with hydrazoic acid in a Mitsunobu reaction to yield the corresponding azides with inversion of configuration at C9. In situ reduction of these azides provided 9-amino(9-deoxy)epicinchonine and 9-amino(9-deoxy)epiquinine, respectively. The structures were confirmed by CD-spectroscopy and X-ray crystallography.
108 citations