Enantioselective preparation of 3,4,5-trisubstituted-4,5-dihydroisoxazoles and 4-substituted-5,6-dihydro-4H-[1,2]-oxazines by nitrile oxide cycloaddition to α-silyl allyl alcohols

Kamimura, Akio; Kaneko, Yukio; Ohta, A.; Kakehi, Akikazu; Matsuda, Hirokazu; Kanemasa, Shuji

doi:10.1016/s0040-4039(99)00688-7

Cited by 15 publications

(8 citation statements)

References 31 publications

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“…In search of new chiral Lewis acid catalysts we examined participation of lanthanides, metals of strong oxophilicity which due to large ionic radii (1.1 -0.9 Å) show high coordination numbers (6)(7)(8)(9)(10)(11)(12) [32]. These catalysts were successfully applied in asymmetric 1,3dipolar cycloaddition of nitrones and alkenes in the presence of chiral amines and/or phenols [14,33].…”

Section: Resultsmentioning

confidence: 99%

“…Several obstacles such as propensity of nitrile oxides to dimerize and form unreactive complexes with metal catalysts as well as interaction of tertiary amines used to generate nitrile oxides with Lewis acids had to be overcome [5]. Cycloaddition of the nitrile oxides to the optically active internal -silyl allyl alcohols in the presence of alkoxymagnesium bromides afforded trisubstituted 2isoxazolines without loss of chirality [6]. Ukaji et al applied a related approach to the first asymmetric metalcatalyzed 1,3-dipolar cycloaddition reaction of nitrile oxides to -substituted allylic alcohols with diethylzinc and (R,R)-diisopropyl tartrate as the chiral auxiliary [7,8].…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective 1,3‐dipolar cycloaddition reactions using complexes of (−)‐sparteine

Gucma

Golebiewski

2008

Journal of Heterocyclic Chem

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective 1,3‐dipolar cycloaddition reactions using complexes of (−)‐sparteine

Gucma

Golebiewski

2008

Journal of Heterocyclic Chem

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“…SCOE 1 can be obtained by a ring-expansion reaction of some substituted isoxazolines; however, application of such a method is rather restricted. − …”

Section: Synthesis Of Six-membered Cyclic Oxime Ethers 1 Andmentioning

confidence: 99%

“…Apparently, the mechanism of the transformation 81 → 82 includes Si−C bond cleavage in the starting isoxazolines 81 with the fluoride anion to form anions 83 , subsequent isoxazoline ring-opening, and recyclization of arising oxime anions 84 …”

Section: Synthesis Of Six-membered Cyclic Oxime Ethers 1 Andmentioning

confidence: 99%

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Chemistry of Six-Membered Cyclic Oxime Ethers. Application in the Synthesis of Bioactive Compounds

2011

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CONTENTS 1. Introduction 5004 2. Synthesis of Six-Membered Cyclic Oxime Ethers 1 and 2 5005 2.1. [4 þ 2]-Cycloaddition Reactions 5005 2.2. Intramolecular Cyclization of γ-Functionalized Oximes 5009 2.3. Intramolecular Cyclization of Functionalized O-Substituted Hydroxylamines 5012 2.4. Synthesis of SCOE from N-O-Containing Heterocyclic Derivatives 5012 2.4.1. Synthesis of SCOE from Other 1,2-Oxazines 5012 2.4.2. Synthesis of SCOE from Isoxazolines and Five-Membered Cyclic Nitronates 5014 2.5. Other Methods 5014 3. Chemical Properties of SCOE 5016 3.1. Reduction of SCOE 5016 3.1.1. Reduction of SCOE to Tetrahydro-2H-1,2oxazines 5018 3.1.2. Reduction of SCOE with 1,2-Oxazine Ring-Opening 5020 3.1.2.1. Reduction of SCOE to 1,4-Amino Alcohols. 5020 3.1.2.2. Reduction of SCOE to Carbonyl Compounds. 5021 3.1.2.3. Reduction of SCOE to γ-Hydroxyoximes. 5022 3.1.3. Reduction Reactions of SCOE with 1,2-Oxazine Ring Contraction 5022 3.1.3.1. Reduction of SCOE to Pyrrolidines. 5022 3.1.3.2. Reduction of SCOE to N-Hydroxypyrrolidines. 5023 3.1.3.3. Reduction of SCOE to Pyrroles. 5024 3.1.3.4. Reduction of SCOE to Aziridines. 5025 3.1.3.5. Reduction of SCOE to Furan Derivatives. 5025 3.2. Addition Reactions to the CdN Double Bond of SCOE 5026 3.3. 1,2-Oxazine Ring-Opening in SCOE 5027 3.4. Deoximation of SCOE 5028 3.5. 1,2-Oxazine Ring Rearrangements in SCOE 5028 3.6. 1,2-Oxazine Ring Fragmentation Reactions in SCOE 5030 4. SCOE in the Synthesis of Natural Products and Biologically Active Compounds 5031 4.1. Synthesis of Amino Acids 5032 4.2. Synthesis of Polyhydroxylated Pyrrolidines 5033 4.3. Synthesis of Pyrrolizidine and Indolizidine Alkaloids and Their Analogs 5033 4.4. Synthesis of Biologically Active 2-Aryl-Substituted Pyrrolidines and Amines 5035 4.5. Synthesis of Other Natural Compounds 5036 5. Conclusion 5037 Author Information 5037 Biographies 5038 Acknowledgment 5038 References 5038

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ChemInform Abstract: Enantioselective Preparation of 3,4,5‐Trisubstituted‐4,5‐dihydroisoxazoles and 4‐Substituted‐5,6‐dihydro‐4H‐[1,2]‐oxazines by Nitrile Oxide Cycloaddition to α‐Silyl Allyl Alcohols.

et al. 1999

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Enantioselective preparation of 3,4,5-trisubstituted-4,5-dihydroisoxazoles and 4-substituted-5,6-dihydro-4H-[1,2]-oxazines by nitrile oxide cycloaddition to α-silyl allyl alcohols

Cited by 15 publications

References 31 publications

Enantioselective 1,3‐dipolar cycloaddition reactions using complexes of (−)‐sparteine

Enantioselective 1,3‐dipolar cycloaddition reactions using complexes of (−)‐sparteine

Chemistry of Six-Membered Cyclic Oxime Ethers. Application in the Synthesis of Bioactive Compounds

ChemInform Abstract: Enantioselective Preparation of 3,4,5‐Trisubstituted‐4,5‐dihydroisoxazoles and 4‐Substituted‐5,6‐dihydro‐4H‐[1,2]‐oxazines by Nitrile Oxide Cycloaddition to α‐Silyl Allyl Alcohols.

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