2011
DOI: 10.1002/chem.201100019
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Enantioselective Gold‐Catalyzed Functionalization of Unreactive sp3 CH Bonds through a Redox–Neutral Domino Reaction

Abstract: Selectivity is golden: The first asymmetric redox-neutral domino reaction catalyzed by gold that results in the direct functionalization of unreactive sp(3) C-H bonds has been reported. This method consists of a heterocyclization/1,5-hydride transfer/cyclization reaction and provides synthetically valuable azepines with high enantioselectivities and in high yields (Tf = triflate; see scheme).

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Cited by 184 publications
(51 citation statements)
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“…The resulting furanfused azepines 154 could be obtained in good to excellent yields with satisfactory enantioselectivity (Scheme 12.67) [71]. …”
Section: Via Au-catalyzed C(sp 3 )-H Functionalizationmentioning
confidence: 99%
“…The resulting furanfused azepines 154 could be obtained in good to excellent yields with satisfactory enantioselectivity (Scheme 12.67) [71]. …”
Section: Via Au-catalyzed C(sp 3 )-H Functionalizationmentioning
confidence: 99%
“…Transition-metal catalysts such as complexes of gold [132,133] and platinum, [134] as well as those of cobalt [135] and palladium, [136] are used efficiently in cyclization reactions involving the intramolecular [1,5] transfer of a hydride onto a terminal alkyne or an electron-deficient alkene, followed by ring closure on the resulting stabilized carbocation (iminium-type) intermediate (Scheme 61). [132][133][134][135][136] The most typical examples of this internal redox process involve the coupling of C(sp 3 )-H bonds with double bonds (Scheme 61). [133,135,[137][138][139][140][141][142][143][144] In this process, activation of an electron-deficient alkene by a Lewis acid or transition metal initiates a 1,5-hydride transfer and the formation of a stabilized cation, which induces cyclization to form a C-C bond.…”
Section: A-c(sp 3 )-H Bond Functionalization Of Amines Via Transitionmentioning
confidence: 99%
“…[132][133][134][135][136] The most typical examples of this internal redox process involve the coupling of C(sp 3 )-H bonds with double bonds (Scheme 61). [133,135,[137][138][139][140][141][142][143][144] In this process, activation of an electron-deficient alkene by a Lewis acid or transition metal initiates a 1,5-hydride transfer and the formation of a stabilized cation, which induces cyclization to form a C-C bond. This strategy has also been extended to the coupling of C(sp 3 )-H bonds with triple bonds (Scheme 61).…”
Section: A-c(sp 3 )-H Bond Functionalization Of Amines Via Transitionmentioning
confidence: 99%
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“…Examples of intramolecular functionalization initiated by Lewis acids and occurring via hydride shift/ring closure sequences are presented in Ref. [8][9][10].…”
Section: Introductionmentioning
confidence: 99%