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Volumn 72, Issue 4, 2007, Pages 1309-1314

A biocatalytic approach to synthesizing optically active orthogonally protected trans-cyclopentane-1,2-diamine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SUBSTITUENTS; ENZYMATIC REACTION; RACEMIC DIAMINES;

EID: 33846943712     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062205h     Document Type: Article
Times cited : (26)

References (60)
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    • For an excellent review, see: a
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    • For some recent examples of the utility of trans-cyclohexane-1,2- diamine derivatives in asymmetric catalysis, see: (b) Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170-7171.
    • For some recent examples of the utility of trans-cyclohexane-1,2- diamine derivatives in asymmetric catalysis, see: (b) Huang, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 7170-7171.
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    • 0030602167 scopus 로고    scopus 로고
    • For some examples of macrocyclic receptors containing the trans-cyclohexane-1,2-diamine unit, see: f
    • For some examples of macrocyclic receptors containing the trans-cyclohexane-1,2-diamine unit, see: (f) Pan, Z.; Still, W. C. Tetrahedron Lett. 1996, 37, 8699-8702.
    • (1996) Tetrahedron Lett , vol.37 , pp. 8699-8702
    • Pan, Z.1    Still, W.C.2
  • 31
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    • Optically active trans-cyclopentane-1,2-diamine was prepared for the first time by applying the classical recrystallization with tartaric acid. However, high enantiomeric excesses were obtained only after several recrystallization cycles, which led to a low overall yield: Toftlund, H.; Pedersen, E. Acta Chem. Scand. 1972, 26, 4019-4030.
    • Optically active trans-cyclopentane-1,2-diamine was prepared for the first time by applying the classical recrystallization with tartaric acid. However, high enantiomeric excesses were obtained only after several recrystallization cycles, which led to a low overall yield: Toftlund, H.; Pedersen, E. Acta Chem. Scand. 1972, 26, 4019-4030.
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    • Du, B.1    Daisy, J.J.2
  • 44
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    • Synthesized by ring opening of cyclopentene oxide with the corresponding secondary amine: González-Sabín, J.; Rebolledo F.; Gotor, V. Biotechnol. J. 2006, 1, 835-841.
    • Synthesized by ring opening of cyclopentene oxide with the corresponding secondary amine: González-Sabín, J.; Rebolledo F.; Gotor, V. Biotechnol. J. 2006, 1, 835-841.
  • 46
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    • We chose acetamide 3a instead of diamine 1a due to the clearer 1H NMR spectrum
    • 1H NMR spectrum.
  • 57
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    • Allyl group was selectively removed employing a Pd(0) catalyst and mercaptobenzoic acid as allyl group scavenger: Lemaire-Audoire, S.; Savignac, M.; Genêt, J. P. Tetrahedron Lett. 1995, 36, 1267-1270.
    • Allyl group was selectively removed employing a Pd(0) catalyst and mercaptobenzoic acid as allyl group scavenger: Lemaire-Audoire, S.; Savignac, M.; Genêt, J. P. Tetrahedron Lett. 1995, 36, 1267-1270.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.