- Lithium perchlorate mediated three component reaction for the preparation of primary amines
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In the presence of lithium perchlorate in diethyl ether, LPDE, a three- component reaction between aldehydes, sodium hexamethyldisilazane or lithium hexamethyldisilazane, LHMDS, and different nucleophiles proceeds smoothly to afford primary amines in good yields.
- Saidi, Mohammad R.,Javanshir, Shahrzad,Mojtahedi, Mohammad M.
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- Enantio- and Diastereoselective Synthesis of 1,5-syn-(Z)-Amino Alcohols via Imine Double Allylboration: Synthesis of trans-1,2,3,6-Tetrahydropyridines and Total Synthesis of Andrachcine
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A stereoselective synthesis of trans-1,2,3,6-tetrahydropyridines 8 is described. This synthesis proceeds via intramolecular Mistunobu reactions of 1,5-syn-(Z)-amino alcohols 7, which were prepared by a highly diastereo- and enantioselective double-allylboration reaction of aldehyde 5 and silylimine 6. The chiral bifunctional γ-borylallylborane 9E was generated in situ by hydroboration of allene 3 with (diisopinocampheyl)borane 4. This strategy was applied to the total synthesis of andrachcine 1, thus establishing with certainty the absolute and relative configuration of the natural product.
- Allais, Christophe,Roush, William R.
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supporting information
p. 2646 - 2649
(2017/05/24)
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- Access to nitriles from aldehydes mediated by an oxoammonium salt
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A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.
- Kelly, Christopher B.,Lambert, Kyle M.,Mercadante, Michael A.,Ovian, John M.,Bailey, William F.,Leadbeater, Nicholas E.
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supporting information
p. 4241 - 4245
(2015/04/14)
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- Asymmetric synthesis of propargylamides via 3,3′-disubstituted binaphthol-modified alkynylboronates
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(Chemical Equation Presented) Alkynylboronates derived from 3,3′-disubstituted-2,2′-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective s
- Wu, T. Robert,Chong, J. Michael
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- Lithium perchlorate mediated three-component preparation of primaryaminoesters
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A three-component reaction between an aldehyde, metallated hexamethyldisilazane and a functionalized organozinc compound proceeded smoothly in the presence of LiClO4 in diethyl ether to afford primary amino esters in good yields.
- Saidi, Mohammad R.,Azizi, Najmoddin
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- Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of (±)-thienamycin
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The lithium enolate Z-11 derived from methyl 3-dimethyl(phenyl)silylbutanoate reacts with the N-silylimines of cinnamaldehyde 12, of 3-trimethylsilylpropynal 18, and of 3-trimethylsilylpropenal 19 to give β-lactams with a high level of stereoselection in
- Fleming, Ian,Kilburn, Jeremy D.
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p. 2663 - 2671
(2007/10/03)
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- DIASTEREOSELECTIVE INTRAMOLECULAR DIELS-ALDER RECTION OF N-ALKOXYCARBONYL-1-AZA-1,3-BUTADIENES AND A TOTAL SYNTHESIS OF THE PIPERIDINE ALKALOID, (+/-)-SEDRIDINE
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Total synthesis of (+/-)-sedridine, the piperidine alkaloid, was accomplished on the basis of diastereoselective intramolecular Diels-Alder reaction of the ψ',ω'-unsaturated N-alkoxycarbonyl-1-aza-1,3-butadiene generated in situ from N-trimethylsilyl-1-az
- Uyehara, Tadao,Chiba, Naoki,Suzuki, Ichiro,Yamamoto, Yoshinori
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p. 4371 - 4374
(2007/10/02)
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- AN ENANTIOSELECTIVE APPROACH TO CARBAPENEM ANTIBIOTICS: FORMAL SYNTHESIS OF (+)-THIENAMYCIN
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An enantioselective synthesis of intermediates in synthesis of thienamycin (15) and epithienamycin-C (16) is described.
- Hart, David J.,Ha, Deok-Chan
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p. 5493 - 5496
(2007/10/02)
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- Preparation of Primary Amines and 2-Azetidinones via N-Trimethylsilyl Imines
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Nonenolizable aldehydes react with lithium bis(trimethylsilyl)amide at ambient temperatures to afford solutions of N-trimethylsilyl aldimines.Treatment of these solutions with Grignard reagents or alkyllithiums followed by an aqueous workup gives primary amines in moderate to excellent yields.Treatment of N-trimethylsilyl aldimines with ester enolates provides an expedient route to 1-unsubstituted 2-azetidinones.
- Hart, David J.,Kanai, Ken-ichi,Thomas, Dudley G.,Yang, Teng-Kuei
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p. 289 - 294
(2007/10/02)
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