Fluorous scavenger for parallel preparation of tertiary sulfonamides leading to secondary amines

Baslé, Emmanuel; Jean, Mickaël; Gouault, Nicolas; Renault, Jacques; Uriac, Philippe

doi:10.1016/j.tetlet.2007.09.110

Cited by 13 publications

(3 citation statements)

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“…However, it was found that the classical reagent system Ph 3 P−DIAD was better than the fluorous one in these cases. Use of the same fluorous phosphine was also reported by Zhang and Lu in the same year for automatic (96 parallel reactions) fluorous solid phase extraction in Mitsunobu esterification/etherification/ N -alkylation. , In the alkylation of various 2-nitrobenzenesulfonyl-substituted sulfonamides (using PS−PPh 3 −DTBAD), use of a fluorous scavenger C 8 F 17 CH 2 CH 2 CH 2 I has been reported by Baslé et al to facilitate the isolation of amine products . A nice review by Zhang and Curran on fluorous solid-phase separation has also appeared recently .…”

Section: Modification Of Mitsunobu Protocolmentioning

confidence: 85%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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His research interests include Organophosphorus Chemistry and Main Group Chemistry. He has over 115 publications so far and is a fellow of the Indian Academy of Sciences, Bangalore. N. N. Bhuvan Kumar was born in Cherukupalli, Guntur, India. After completing his B.Sc. from Nagarjuna University, he joined the School of Chemistry, University of Hyderabad, as a postgraduate student in the year 2000 and obtained his Master's degree in Chemistry. Currently, he is pursuing a Ph.D. on Organophosphonates under the supervision of Prof. K. C. Kumara Swamy. E. Balaraman was born in Kancheepuram, Chennai, India, in 1980. He received his M.Sc. in Chemistry from Vivekananda College [Madras University (2002)] and his Ph.D. degree in the areas of organophosphonates and modified BINOLs under the guidance of Prof. K. C. Kumara Swamy. Presently he is a postdoctoral fellow with Professors David Milstein and Ronny Neumann at the Weizmann Institute of Science, Israel. K. V. P. Pavan Kumar was born in Hyderabad (Andhra Pradesh), India, in 1979. He obtained his B.Sc. (Chemistry Honors) and M.Sc. (Chemistry) degrees from Sri Sathya Sai Institute of Higher Learning, Puttaparthi, A.P., India. He obtained his Ph.D. degree under the guidance of Prof. K. C. Kumara Swamy in October 2006. Presently he is working as a postdoctoral fellow in the area of hydroamination reactions using new titanium catalysts with Prof. Pierre Le Gendre at the Universite ´de Bourgogne, France.

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Section: Modification Of Mitsunobu Protocolmentioning

confidence: 85%

Mitsunobu and Related Reactions: Advances and Applications

et al. 2009

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“…0, 135.8, 134.1, 133.6, 132.9, 131.2, 128.8, 128.2, 128.0, 125.4, 48. Analytical data are consistent with those reported in the literature. 16…”

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A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides

Beisel

Manolikakes

2015

Synthesis

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“…Alternatively, formal nucleophilic substitution can also be achieved via a 1,2-elimination to generate a cyclopropene intermediate, followed by addition of a nucleophile across the strained double bond (eq ). The latter transformation proceeds readily in the presence of vicinal electron-withdrawing groups; however, unsubstituted cyclopropyl halides have been shown to undergo this reaction as well, producing useful cyclopropanol and cyclopropylamine derivatives. However, the majority of the known reactions of this type (eq ) either are nonselective due to harsh reaction conditions or have no potential selectivity issues, with only a handful of examples showing good site- or facial differentiations in polycyclic substrates where selectivity of addition is imparted by excessive rigidity and bulk .…”

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Highly Diastereoselective Formal Nucleophilic Substitution of Bromocyclopropanes

et al. 2009

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A highly diastereoselective formal nucleophilic substitution of bromocyclopropanes with oxygen- and nitrogen-based nucleophiles was demonstrated. The reaction proceeds via a base-assisted dehydrohalogenation producing a cyclopropene intermediate, which subsequently undergoes addition of a pronucleophile across the strained double bond. Very high chemoselectivity toward addition of primary and secondary alkoxides, as well as N-nucleophiles, in the presence of tert-butoxide base was observed, whereas phenoxides did not undergo addition under these reaction conditions. Facial selectivity of the addition can be efficiently controlled either by sterics or through a directing effect of an amide, carboxylate, and an o-aminomethylphenol function. Employment of tethered optically active amino alcohols as pronucleophiles allowed for efficient assembly of homochiral bicyclic compounds.

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Fluorous scavenger for parallel preparation of tertiary sulfonamides leading to secondary amines

Cited by 13 publications

References 14 publications

Mitsunobu and Related Reactions: Advances and Applications

Mitsunobu and Related Reactions: Advances and Applications

A Palladium-Catalyzed Three-Component Synthesis of Arylmethylsulfonamides

Highly Diastereoselective Formal Nucleophilic Substitution of Bromocyclopropanes

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