Stereoselective nucleophilic substitution of 6-methoxy-1-methoxycarbonylpipecolate: enantioselective synthesis of (+)-sedamine from L-lysine

Irie, Kunihiko; Aoe, Keiichi; Tanaka, Takeshi; Saito, Shôichi

doi:10.1039/c39850000633

Cited by 51 publications

(14 citation statements)

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“…An identical conformation is also found in the structure of the following piperidine compounds having an N-carbonyl and an a-amino ester function: the cis and trans isomers of N- [(tert-butyloxy)carbonyl]-4-methyl-4-phenylpipecolic acid (Sugg, Griffin & Portoghese, 1985) and 6-phenylcarbamoylpipecolate (Irie, Aoe, Tanaka & Saito, 1985). In (3) both the methyl ester at C2 and the vinyl group at C3 are found in the equatorial position.…”

Section: Commentmentioning

confidence: 66%

One Bicyclic β-Lactam and Two Bicyclic γ-Lactam Compounds

Ridder¹,

Reiss²,

Schenk³

et al. 1996

Acta Crystallogr C

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Data collection: XSCANS (Fait, 1991 (Received 19 May 1995; accepted 27 October 1995) AbstractThe crystal structures of the bicyclic /3-1actam, rac-( 2R*,4S*,6S* )-4-chloro-4-methyl-8-oxo-1-azabicyclo[4.2.0]octane-2-carboxylic acid methyl ester, CIoH14C1NO3 (1), and the bicyclic 7-1actams, rac-(5R*,7S*,9S*)-7-chloro-7-methyl-3-oxooctahydroindolizine-5-carboxylic acid methyl ester, C11HI6CINO3 (2), and rac-(5R* , 6S*, 10R*)-3-oxo-6-vinyloctahydro-lHpyrrolo[1,2-a]azepine-5-carboxylic acid methyl ester, C13HI9NO3 (3), have been established by X-ray crystallography. In (1) and (2) the a-amino ester function and the CI atom occupy an axial position in a chair-like piperidine ring. In (3) the methyl ester and the vinyl group are equatorially placed on the chair-like sevent Present address: European Commission, Institute for Transuranium Elements,

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Section: Commentmentioning

confidence: 66%

One Bicyclic β-Lactam and Two Bicyclic γ-Lactam Compounds

Ridder¹,

Reiss²,

Schenk³

et al. 1996

Acta Crystallogr C

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“…The high stereoselectivity observed in the reactions of a-methoxy-N-acylpiperidines with nucleophiles is now well documented (3,7,8): the cis stereochemistry results from stereoelectronically preferred axial attack of the nucleophile on the irninium intermediate that contains the phenethyl chain in the axial orientation due to A ' ,~ strain.…”

Section: Resultsmentioning

confidence: 99%

Sedum alkaloids XII. Synthesis of the new piperidine alkaloids homosedinone and dihomosedinone

Durant¹,

Hootelé²

1992

Can. J. Chem.

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The new piperidine alkaloids homosedinone 2 and dihomosedinone 3 , isolated from Sedum acre, have been synthesized from (-)-norsedamine 7 by application of the sequence: anodic methoxylation -elimination -nucleophilic addition.ALEX DURANT et CLAUDE HOOTELE. Can. J. Chem. 70, 2722 (1992).La synthbse de deux nouveaux alcaloldes pipiridiniques, I'homosCdinone 2 et la dihomoskdinone 3 , isolCs de Sedum acre, est dCcrite au depart de la (-)-norsCdamine 7 par application de la sequence : mCthoxylation anodiqueClimination -addition nuclCophile.

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“…Electrochemical oxidation (Irie et al, 1985) of the protected L-lysine derivative 5 gives piperidine 6, suitable for acyliminium chemistry in the 6-position of the heterocyclic ring (Fig. 4).…”

Section: Hemisyntheses From C~-amino Acidsmentioning

confidence: 99%