Efficient Synthesis of (±)-N-Boc-pregabalin via Hetero-Diels-Alder Addition of Methyl 3-Nitrosoacrylate to Ethyl Vinyl Ether

Gallos, John K.; Alexandraki, Elli S.; Stathakis, Christos I.

doi:10.3987/com-07-10994

Cited by 14 publications

(7 citation statements)

References 26 publications

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“…Sodium cyanoborohydride in acetic acid is a common reagent. Under such conditions, various dihydrooxazines 1 are smoothly transformed to the corresponding tetrahydro-2 H -1,2-oxazines 103 (Scheme ). ,,,,,,,− This reaction usually proceeds with high stereoselectivity and in high yields . Many functional groups in the 1,2-oxazine ring, in particular an ester group, remain intact during the reduction.…”

Section: Chemical Properties Of Scoementioning

confidence: 99%

“…Transformation of SCOE to pyrrolidines can be performed stepwise with the reverse order of reduction of the bonds in the oximino group, i.e. reducing first the CN bond with sodium cyanoborohydride or borane−tetrahydrofuran complex and hydrogenating the N−O bond in the resulting tetrahydrooxazine 103 (see Scheme ). ,− In this case, the formation of pyrroles as side products is not possible. In addition, such a procedure is more preferable for the stereoselective formation of a new stereocenter at C-2 of the pyrrolidine ring.…”

Section: Chemical Properties Of Scoementioning

confidence: 99%

“…SCOE containing ester or carboxy groups are considered as convenient precursors of various natural and unnatural amino acids, which are of interest for the synthesis of modified peptides and as pharmaceutical drugs with a wide range of biological activity. ,,,,− ,, …”

Section: Scoe In the Synthesis Of Natural Products And Biologically A...mentioning

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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Section: Chemical Properties Of Scoementioning

confidence: 99%

Section: Chemical Properties Of Scoementioning

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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“…(AE)-N-Boc-pregabalin has been synthesized in low overall yields via a heteroDiels-Alder addition of 3-nitrosoacrylate to ethyl vinyl ether [57]. D-Mannitol has also been used as the primary source of chirality in a high-yielding (28% overall yield), multistep synthesis of (S)-pregabalin (5) [58].…”

Section: Pregabalinmentioning

confidence: 99%

Synthesis of γ‐Aminobutyric Acid Analogs

Hanrahan

Johnston

2009

Amino Acids, Peptides and Proteins in Organic Chemistry

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“…. 3H 2 O και K 2 S 2 O 8 ,18 με ΙΒΧ,19 ι με KMnO 4 δεν είχαν επιτυχία. Πταν όμωσ χρθςιμοποιικθκε PDC20 παρατθρικθκε ςτο ΤLC θ πρϊτθ φλθ να μετατρζπεται ςε μια άπολθ ζνωςθ, τθσ οποίασ θ ταυτοποίθςθ ζγινε με 1 Θ-ΝΜR και βρζκθκε να είναι θ αλδεψδθ.…”

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Στερεοεκλεκτική Σύνθεση Ετεροκυκλικών Φυσικών Προϊόντων Και Αναλόγων Τους

Kanakis¹,

Κανάκης²

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Efficient Synthesis of (±)-N-Boc-pregabalin via Hetero-Diels-Alder Addition of Methyl 3-Nitrosoacrylate to Ethyl Vinyl Ether

Cited by 14 publications

References 26 publications

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

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

Synthesis of γ‐Aminobutyric Acid Analogs

Στερεοεκλεκτική Σύνθεση Ετεροκυκλικών Φυσικών Προϊόντων Και Αναλόγων Τους

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