Enantioselective Kita Oxidative Spirolactonization Catalyzed by In Situ Generated Chiral Hypervalent Iodine(III) Species

Uyanik, Muhammet; Yasui, Takeshi; Ishihara, Kazuaki

doi:10.1002/anie.200907352

Cited by 434 publications

(150 citation statements)

References 25 publications

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“…197 This method is not only notable in that it is metal-free and practical, requiring only two components, but is the first example of intermolecular, enantioselective alkene diamination. Employing Ishihara’s C 2 -symmetric chiral iodane 280 (Scheme 71) 198 and bismesylide ( 278 ) as the nitrogen source, alkenes underwent addition to form diamines 279 with good yields and high asymmetric induction. In all but a few cases, the crystallinity imparted by the bissulfonyl groups facilitates purification of these products to enantiomeric purity by a single recrystallization.…”

Section: Hypervalent Iodine Reagentsmentioning

confidence: 99%

Methods for direct alkene diamination, new & old

2012

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The 1,2-diamine moiety is a ubiquitous structural motif present in a wealth of natural products, including non-proteinogenic amino acids and numerous alkaloids, as well as in pharmaceutical agents, chiral ligands and organic reagents. The biological activity associated with many of these systems and their chemical utility in general has ensured that the development of methods for their preparation is of critical importance. While a wide range of strategies for the preparation of 1,2-diamines have been established, the diamination of alkenes offers a particularly direct and efficient means of accessing these systems. The purpose of this review is to provide an overview of all methods of direct alkene diamination, metal-mediated or otherwise.

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Section: Hypervalent Iodine Reagentsmentioning

confidence: 99%

Methods for direct alkene diamination, new & old

2012

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“…Reaction of enones such as 59 with the modified Fujita reagent 60 developed by Ishihara and coworkers [14] transforms them into α-substituted ketones 61 as shown in Scheme 18 [15]. Although yields are higher when chalcones are employed, the reaction also proceeds with aliphatic ketones (R ¼ Me, 10%) and esters (R ¼ OMe, 12%, 96% ee).…”

Section: Stereoselective Pathwaymentioning

confidence: 97%

Rearrangements Induced by Hypervalent Iodine

Maertens

Canesi

2015

Topics in Current Chemistry

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This chapter describes advances in hypervalent iodine(III)-induced rearrangements reported between 2004 and 2015, beginning with Hofmann-type rearrangements and aliphatic aryl transpositions. In both reactions the iodine(III) reagent may be off-the-shelf or catalytically generated in situ. A number of stereoselective transformations are discussed, followed by transpositions triggered through phenol dearomatization, including Wagner-Meerwein-type rearrangements, Prins-pinacol transpositions, and a tandem polycylization-pinacol process. Other rearrangements such as an iodonio-Claisen rearrangement, an ipso-rearrangement, and rearrangements performed using iodine(V) are also described.

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“…1 Therefore, our formulative ideas centered upon developing more utilitarian diastereoselective dearomatization processes. 6 We imagined some hypervalent I (III) reagent prompted oxidative dearomatization involving an unprecedented ortho -cyclization of a lactic acid derived tether should produce a family of sturdy cyclohexadienones capable of further regioselective and diastereoselective reactions.…”

Section: The Planmentioning

confidence: 99%

Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

et al. 2010

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The oxidative dearomatization of resorcinol derivatives, which are outfitted with a lactic acid derived chiral tether, and mitigated by hypervalent iodine derivatives of PhIO, affords stable chiral cyclohexadienones as useful building blocks for the construction of many highly functionalized chiral six and seven-membered ring systems. Herein, we report a multitude of remarkable and unexpected diastereoselective transformations stemming from these cyclohexadienone adducts.

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Enantioselective Kita Oxidative Spirolactonization Catalyzed by In Situ Generated Chiral Hypervalent Iodine(III) Species

Cited by 434 publications

References 25 publications

Methods for direct alkene diamination, new & old

Methods for direct alkene diamination, new & old

Rearrangements Induced by Hypervalent Iodine

Dearomatization applications of I(III) reagents and some unusual reactivity amongst resorcinol derived cyclohexadienones

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