Ring closing metathesis of α- and β-amino acid derived dienes

Gardiner, James; Aitken, Steven G.; McNabb, Stephen B.; Zaman, Shazia; Abell, Andrew D.

doi:10.1016/j.jorganchem.2006.09.061

Cited by 13 publications

(4 citation statements)

References 48 publications

(69 reference statements)

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“….9 Hz, 3 H; CH 3 ), 0.21 ppm (s, 9 H; CH 3 ); 13 C NMR (50 MHz, CDCl 3 , 258C, TMS): d = 166.9 (2C), 133.9 (2C), 131.4 (2C), 123.3 (2C), 101.9, 86.7, 41.9, 40.6, 27.7, 26.0, 25.1 (2C), 0.12 ppm (3C); GC-MS: m/z (%): 313(6) [M + ], 298 (28), 270 (21), 256 (100), 204(70), 130 (55), 102 (19), 73 (24); elemental analysis calcd (%) for C 18 H 23 NO 2 Si: C 68.97, H 7.40, N 4.47; found: C 69.49, H 7.65, N 4.19. Analytical HPLC: Chiracel OD-H column (250 4 mm, Daicel), eluent: iPrOH/hexane (1:99), flow rate: 1 mL min À1 , UV detection at 254 nm; t r (R enantiomer) = 13.57 min, t R (S enantiomer) = 14.21 min: e.r.…”

Section: -[(1smentioning

confidence: 99%

“…= 4:96. (34), 185 (100), 157 (28), 142 (62), 130 (29), 104 (24), 76 (22); elemental analysis calcd (%) for C 19 H 15 NO 2 : C 78.87, H 5.23, N 4.84; found: C 78.99, H 6.61, N 4.49. Analytical HPLC: Chiralpack AD-H column (250 4 mm, Daicel), eluent: iPrOH/hexane (10:90), flow rate: 1 mL min À1 , UV detection at 254 nm; t r (R enantiomer) = 13.90 min: e.r.…”

Section: -[(1smentioning

confidence: 99%

“…The unsaturated b 3 -amino acid derivatives 6 c ( Table 2) and 10 have reactive side chains that could be used for a range of synthetic transformations. [28,29] The reaction of 6 i with an excess of m-chloroperoxybenzoic acid (m-CPBA) in tetrahydrofuran and in the presence of potassium hydrogen phosphate [30] gave the corresponding selenone 11. This is a valuable synthetic intermediate because of the excellent leaving group ability of the selenonyl group in nucleophilic substitution reactions.…”

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Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Temperini

Terlizzi

Testaferri

et al. 2009

Chemistry A European J

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A stereospecific synthesis of beta(3)-amino acids has been accomplished starting from readily available and enantioenriched propargylic alcohols. This conversion can be effected in only three steps by selenium-mediated organic transformations of the carbon-carbon triple bond. This method is especially attractive because the reactive Se-phenyl selenocarboxylate intermediates can be trapped with the amine functionality of an amino acid derivative. Through this strategy a chain elongation at the N-terminus has been effected. The N-deprotection and repetition of the homologation with other Se-phenyl selenocarboxylate intermediates produced beta- and mixed alpha/beta-oligopeptides without the use of coupling agents.

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Section: -[(1smentioning

confidence: 99%

Section: -[(1smentioning

confidence: 99%

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confidence: 99%

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Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Temperini

Terlizzi

Testaferri

et al. 2009

Chemistry A European J

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“…However, in no case could the envisaged ring structure be obtained in good yields, and mainly starting material and decomposition products were observed. It is known that the introduction of extra substituents in the aliphatic part increases the viability for ring closure during RCM . Therefore, further studies were evaluated on α-amino acid derivatives 3a – i .…”

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Synthesis of Fused 3-Aminoazepinones via Trapping of a New Class of Cyclic Seven-Membered Allenamides with Furan

Schurgers¹,

Brigou²,

Urbańczyk‐Lipkowska

et al. 2014

Org. Lett.

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Novel tricyclic tetrahydroazepinones were synthesized via an in situ Diels-Alder reaction of furan with cyclic allenamides. These reactive intermediates are the first examples of cyclic seven-membered allenamides and were prepared starting from N-(2-chloroallyl)-2-allylglycine derivatives via ring-closing metathesis followed by dehydrochlorination. The trapping of the intermediate cycloallene with furan occurred endo- and regioselectively and provided a convenient entry into new building blocks for medicinal chemistry. The diastereoselectivity of the cycloaddition was confirmed using quantum chemical computations.

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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Ring closing metathesis of α- and β-amino acid derived dienes

Cited by 13 publications

References 48 publications

Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Synthesis of Fused 3-Aminoazepinones via Trapping of a New Class of Cyclic Seven-Membered Allenamides with Furan

Olefin Ring‐Closing Metathesis

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Ring closing metathesis of α- and β-amino acid derived dienes

Cited by 13 publications

References 48 publications

Stereospecific Synthesis of β3‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Stereospecific Synthesis of β3‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Synthesis of Fused 3-Aminoazepinones via Trapping of a New Class of Cyclic Seven-Membered Allenamides with Furan

Olefin Ring‐Closing Metathesis

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Product

Resources

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Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents

Stereospecific Synthesis of β³‐Amino Acid Derivatives from Propargylic Alcohols: Efficient Solution‐Phase Synthesis of Oligopeptides without Coupling Agents