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Volumn 66, Issue 33, 2010, Pages 6349-6357

Highly enantioselective desymmetrizations of meso-anhydrides

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALCOHOL; ALKALOID DERIVATIVE; AMINOALCOHOL; CYCLOHEXANE; CYCLOHEXANE DERIVATIVE; GLUTARIC ANHYDRIDE; NUCLEOPHILE; SUCCINIC ANHYDRIDE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955663850     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.121     Document Type: Article
Times cited : (36)

References (60)
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    • Patents: PCT Int. Appl. WO 2001074741 A2
    • Patents: (b) Deng, L.; Chen, Y.; Tian, S. PCT Int. Appl. WO 2001074741 A2, 2001;
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    • Deng, L.1    Chen, Y.2    Tian, S.3
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    • Chem. Abstr. 135 2001 288345
    • (2001) Chem. Abstr. , vol.135 , pp. 288345
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    • U.S. Patent 20,040,082,809 A1
    • (c) Deng, L.; Chen, Y.; Tian, S. U.S. Patent 20,040,082,809 A1, 2004;
    • (2004)
    • Deng, L.1    Chen, Y.2    Tian, S.3
  • 16
    • 77955657830 scopus 로고    scopus 로고
    • Chem. Abstr. 140 2004 374734
    • (2004) Chem. Abstr. , vol.140 , pp. 374734
  • 41
    • 33645036043 scopus 로고    scopus 로고
    • For straightforward syntheses of such compounds including their resolutions, see
    • For straightforward syntheses of such compounds including their resolutions, see: (a) I. Schiffers, T. Rantanen, F. Schmidt, W. Bergmanns, L. Zani, and C. Bolm J. Org. Chem. 7 2006 2320 2331
    • (2006) J. Org. Chem. , vol.7 , pp. 2320-2331
    • Schiffers, I.1    Rantanen, T.2    Schmidt, F.3    Bergmanns, W.4    Zani, L.5    Bolm, C.6
  • 44
    • 77955653914 scopus 로고    scopus 로고
    • cis-Aminoalcohols were less effective than their trans-counterparts. For example, under standard conditions (1R,2S)-5b led to ent-2a with 28% ee: Dissertation at RWTH Aachen University
    • cis-Aminoalcohols were less effective than their trans-counterparts. For example, under standard conditions (1R,2S)-5b led to ent-2a with 28% ee: Rantanen, T. Dissertation at RWTH Aachen University, 2007.
    • (2007)
    • Rantanen, T.1
  • 45
    • 77955665179 scopus 로고    scopus 로고
    • note
    • Basic extraction of the product followed by acidification and organic extraction yielded in pure product.
  • 46
  • 47
    • 9244231110 scopus 로고    scopus 로고
    • Enantiopure piperidinyl- and morpholinyl-substituted diamines were prepared by resolution with mandelic acid. For the synthesis of the racemate and an alternative method for the resolution, see
    • (b) Enantiopure piperidinyl- and morpholinyl-substituted diamines were prepared by resolution with mandelic acid. For the synthesis of the racemate and an alternative method for the resolution, see: J. Gonzalez-Sabin, V. Gotor, and F. Rebolledo Chem. - Eur. J. 10 2004 5788 5794
    • (2004) Chem. - Eur. J. , vol.10 , pp. 5788-5794
    • Gonzalez-Sabin, J.1    Gotor, V.2    Rebolledo, F.3
  • 48
    • 77955656343 scopus 로고    scopus 로고
    • note
    • 2: 45% ee; MeCN: 14% ee.
  • 50
    • 77955662190 scopus 로고    scopus 로고
    • note
    • When benzylalcohol or ethanol was used instead of methanol similar enantioselectivities were observed, but the reaction rates decreased.
  • 51
    • 0033548378 scopus 로고    scopus 로고
    • For preparations of 2h, 2i, and 2j by enzyme-catalyzed hydrolyses of meso-dimethylesters, see: (a) N.W. Boaz Tetrahedron: Asymmetry 10 1999 813 816
    • (1999) Tetrahedron: Asymmetry , vol.10 , pp. 813-816
    • Boaz, N.W.1
  • 57
    • 77955662475 scopus 로고    scopus 로고
    • note
    • In contrast, this behavior was not observed in quinine-accelerated opening of succinic anhydrides. There, the enantioselectivity increased when more catalyst was used.
  • 58
    • 77955664239 scopus 로고    scopus 로고
    • note
    • 2: 13% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.