Diphenyl 2-pyridylphosphine and di-tert-butylazodicarboxylate:Convenient reagents for the Mitsunobu reaction

Kiankarimi, Mehrak; Lowe, Richard F.; McCarthy, James R.; Whitten, Jeffrey P.

doi:10.1016/s0040-4039(99)00819-9

Cited by 76 publications

(55 citation statements)

References 6 publications

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“…Marcantoni et al 46 utilizaram um derivado da D-(R)-cisteína para preparar um intermediário-chave que foi submetido às condições de Mitsunobu modificadas 47 (Esquema 19).…”

Section: Esquema 1 Esquema 2 Esquemaunclassified

Métodos de preparação de lactonas de anel médio

Longo¹,

Bombonato²,

Ferraz³

2007

Quím. Nova

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“…Marcantoni et al 46 utilizaram um derivado da D-(R)-cisteína para preparar um intermediário-chave que foi submetido às condições de Mitsunobu modificadas 47 (Esquema 19).…”

Section: Esquema 1 Esquema 2 Esquemaunclassified

Métodos de preparação de lactonas de anel médio

Longo¹,

Bombonato²,

Ferraz³

2007

Quím. Nova

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“…This limitation has led to a number of modifications to remove the non-polymer supported byproducts by scavenging or destruction. [48][49][50][51] In those approaches, a second reaction is always needed before purification. The only chromatography-free Mitsunobu reaction that does not require additional reaction after the Mitsunobu transformation has been achieved by the Curran group using a fluorous DEAD reagent and a fluorous phosphine (see Section 2.2.4).…”

Section: Mitsunobu Reactions-thementioning

confidence: 99%

Fluorous Synthesis of Heterocyclic Systems

Zhang

2004

Chem. Rev.

211

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and Ph.D. in 1993 from the University of Pittsburgh under the direction of the late Professor Paul Dowd. After a two-year stay at the same university as a Research Assistant Professor, he joined DuPont in 1995. In early 2001 he moved back to Pittsburgh and was one of the key founding members of Fluorous Technologies, Inc. (FTI). He is now the Director of Discovery Chemistry responsible for the research and development of fluorous technologies for solution-phase synthesis and separations. Over the years, Dr. Zhang has gained both academic and industrial experience. His professional areas of interest include free radical chemistry, heterocyclic chemistry, fluorous chemistry, microwave-assisted organic synthesis, and design and synthesis of drug-like small molecule libraries. He has published over 50 peer-reviewed papers including 2 book chapters and 6 review articles. In recent years he delivered many invited lectures and international conference presentations on fluorous technologies and combinatorial chemistry.

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“…The crude reaction mixture was loaded onto an ArgoPore TM ammonium trifluoroacetate column (ArgoPore-NH 2 is a highly cross-linked macroporous resin) and eluted with dichloromethane. Although the first-pass eluent was free of any phosphorous-containing impurity as assayed by 31 P NMR spectroscopy, it must have been a mixture of the Mitsunobu product and DECH. Further separation of this mixture was not reported.…”

Section: Mitsunobu Reactions With a Crown Ether Tagged Phosphinementioning

confidence: 99%

“…(9)]. [31] For example, when this reagent combina- tion was used to couple 3-chloro-5-methoxyphenol and benzylalcohol, the desired product could be isolated free from reagent byproducts after treating the crude reaction mixture with 4 m HCl. Di-tert-butoxycarbonylhydrazine decomposes under acidic conditions to give gaseous isobutylene and carbon dioxide, and water-soluble hydrazine.…”

Section: Mitsunobu Reactions On Polymer-supported Substratesmentioning

confidence: 99%

Separation‐Friendly Mitsunobu Reactions: A Microcosm of Recent Developments in Separation Strategies

Dandapani

Curran

2004

Chemistry A European J

122

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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.

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Diphenyl 2-pyridylphosphine and di-tert-butylazodicarboxylate:Convenient reagents for the Mitsunobu reaction

Cited by 76 publications

References 6 publications

Métodos de preparação de lactonas de anel médio

Métodos de preparação de lactonas de anel médio

Fluorous Synthesis of Heterocyclic Systems

Separation‐Friendly Mitsunobu Reactions: A Microcosm of Recent Developments in Separation Strategies

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