Indium(III) chloride-catalyzed Mukaiyama–Michael addition: synthesis of 2,6-anti-tetrahydropyrans

Chua, Sin‐Siu; Alni, Anita; Chan, Li‐Ting Jocelyn; Yamane, Masaaki; Loh, Teck‐Peng

doi:10.1016/j.tet.2011.04.101

Cited by 18 publications

(10 citation statements)

References 19 publications

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“…InCl 3 supported on silica gel has been used for electrophilic amination of arenes with diethyl azodicarboxylate [16] . Different name reactions such as hetero Diels‐Alder reaction, [17] Aza‐Diels‐Alder reaction, [18] Biginelli reaction, [19] Mukaiyama aldol reaction in water, [20] Michael reaction, [21] Mukaiyama‐Michael reaction, [22] and double Mannich reaction [23] has also been studied with indium(III) chloride. Azedolysis of α,β‐epoxy carboxylic acid with NaN 3 , [24] Polymerization, [25] cyclisation, [26] ring opening reaction of chalcone epoxides with indole and pyrrole [27] are the most important reactions in organic synthesis promoted by InCl 3 .…”

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confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

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This review summarizes recent advances of indium trichloride catalyzed synthesis of different organic compounds. It is obvious that InCl3 co‐ordinates with C−C and/or C‐heteroatom multiple bonds and thereby makes them very prone to nucleophilic attack to form a new bond. This Lewis acid catalyst also activates oxiranes to produce aldehydes. Multicomponent synthesis including C−C bond formation reaction and construction of N, O and S‐containing heterocycles are discussed in organic solvents as well as in water. This article highlights recent developments and application of indium(III) chloride as a catalyst in organic synthesis from 2015 to 2020. The mechanism of few important reactions is discussed in detail which will be very useful for the readers.

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Section: Introductionmentioning

confidence: 99%

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Datta

2021

ChemistrySelect

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“…20,23 Lastly, a Mukaiyama-Michael addition proceeded to afford 14 with 10:1 diasteromeric ratio. 23,24 Notably, while many synthetic methods exist for cis -2,6-tetrahydropyran structures, 25 there are far fewer preparations for trans -2,6-tetrahydropyrans. 26…”

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confidence: 99%

An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

et al. 2018

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An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.

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“…To investigate the utility of α-alkylidene β-oxo phosphates and phosphine oxides, compounds 1a and 1b were prepared from 6-bromo-1,4-dioxa-spiro[4.4]non-6-ene, and 1c was prepared according to reported methods . Silyl enol ether 2 was used in this study since the product derived from 2 was expected to be useful in a variety of transformations such as the Fukuyama reduction and the Liebeskind–Srogl coupling reaction …”

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confidence: 99%

“…All of the reactions using Cu(BF 4 ) 2 (Table , entry 2), Cu(PF 6 ) 2 (Table , entry 3), and Cu(SbF 6 ) 2 (Table , entry 4) afforded 3c in excellent yields; however, the ee was low in all cases when compared with the reaction using Cu(OTf) 2 (Table , entry 1). The reason for this low ee could be attributed to a background reaction, which was proposed to proceed due to catalysis by a silyl cation generated from silyl enol ether 2 .…”

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Enantioselective Mukaiyama–Michael Reaction of Cyclic α-Alkylidene β-Keto Phosphine Oxide and Phosphonate and Asymmetric Synthesis of (R)-Homosarkomycin

et al. 2017

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The asymmetric Mukaiyama-Michael reaction of cyclic α-alkylidene β-oxo phosphates and phosphine oxides that proceeds in a highly enantioselective manner is described. It is possible to carry out these reactions using a catalytic amount of a bisoxazoline-Cu(II) complex without decreasing the enantioselectivity, and one of the products has been successfully used for the first enantioselective synthesis of (R)-homosarkomycin.

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Indium(III) chloride-catalyzed Mukaiyama–Michael addition: synthesis of 2,6-anti-tetrahydropyrans

Cited by 18 publications

References 19 publications

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

Recent Advances of Indium(III) Chloride Catalyzed Reactions in Organic Synthesis

An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

Enantioselective Mukaiyama–Michael Reaction of Cyclic α-Alkylidene β-Keto Phosphine Oxide and Phosphonate and Asymmetric Synthesis of (R)-Homosarkomycin

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