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Volumn 125, Issue 2, 2003, Pages 428-436

Opening of tartrate acetals using dialkylboron bromide: Evidence for stereoselectivity downstream from ring fission

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Indexed keywords

ELIMINATION PROTOCOL;

EID: 0346035731     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja012530g     Document Type: Article
Times cited : (20)

References (47)
  • 15
    • 0346793861 scopus 로고    scopus 로고
    • note
    • Sammakia observed high selectivity when Lewis acid was added slowly and when milder Lewis acids were used.
  • 24
    • 0346793860 scopus 로고    scopus 로고
    • note
    • Crystallographic analysis of the minor isomer (22b) indicated that the thiol addition had occurred with the same facial selectivity as was the case for the cuprate addition (see Supporting Information).
  • 26
    • 0001948147 scopus 로고
    • Kusuda, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2945. For a review, see: Soderquist, J. A. Aldrichimica Acta 1991, 24, 15.
    • (1991) Aldrichimica Acta , vol.24 , pp. 15
    • Soderquist, J.A.1
  • 27
    • 0010640653 scopus 로고
    • The corresponding D-tartrate acetals produced secondary alcohols with S configurations
    • The absolute configuration of the final products was assigned by correlation to literature values of specific rotation or by the preparation of Mosher esters and comparison of the resulting NMR spectra with those of authentic samples prepared from commercially available chiral alcohols (Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549). The corresponding D-tartrate acetals produced secondary alcohols with S configurations.
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 28
    • 0348054850 scopus 로고    scopus 로고
    • note
    • For complete results, see Supporting Information.
  • 31
    • 0347424411 scopus 로고    scopus 로고
    • note
    • 2 at -78 °C, and the samples were monitored by NMR at various probe temperatures.
  • 32
    • 0346163363 scopus 로고    scopus 로고
    • note
    • 2 gave a 7:1 mixture of 32a:32b, indicating that the same facial bias was maintained with the acyclic acetal system.
  • 35
    • 0347424410 scopus 로고    scopus 로고
    • note
    • 2) was used as an external reference.
  • 36
    • 84903270801 scopus 로고
    • 2 (neat): 31.5. (a) Nöth, H.; Vahrenkamp, H. Chem. Ber. 1966, 99, 1049-1067. (b) Dahlhoff, W. V.; Köster, R. Liebigs Ann. Chem. 1975, 1625-1636.
    • (1966) Chem. Ber. , vol.99 , pp. 1049-1067
    • Nöth, H.1    Vahrenkamp, H.2
  • 37
    • 84915135619 scopus 로고
    • 2 (neat): 31.5. (a) Nöth, H.; Vahrenkamp, H. Chem. Ber. 1966, 99, 1049-1067. (b) Dahlhoff, W. V.; Köster, R. Liebigs Ann. Chem. 1975, 1625-1636.
    • (1975) Liebigs Ann. Chem. , pp. 1625-1636
    • Dahlhoff, W.V.1    Köster, R.2
  • 41
    • 0348054829 scopus 로고    scopus 로고
    • note
    • 2-BBr used to open the acetal.
  • 42
    • 0346163361 scopus 로고    scopus 로고
    • note
    • We used the largest experiment error to construct a "window" within which calculated curves were accepted.
  • 43
    • 0025780257 scopus 로고
    • This type of enhancement, where selectivity is generated on two or more levels, has been more rigorously described. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515. See also: Ward, D. E.; Liu, Y.; Rhee, C. K. Synlett 1993, 561-563.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 477-515
    • Buschmann, H.1    Scharf, H.-D.2    Hoffmann, N.3    Esser, P.4
  • 44
    • 0002889946 scopus 로고
    • This type of enhancement, where selectivity is generated on two or more levels, has been more rigorously described. Buschmann, H.; Scharf, H.-D.; Hoffmann, N.; Esser, P. Angew. Chem., Int. Ed. Engl. 1991, 30, 477-515. See also: Ward, D. E.; Liu, Y.; Rhee, C. K. Synlett 1993, 561-563.
    • (1993) Synlett , pp. 561-563
    • Ward, D.E.1    Liu, Y.2    Rhee, C.K.3
  • 45
    • 0348054849 scopus 로고    scopus 로고
    • note
    • General experimental comments, physical properties, and analytical data are given in Supporting Information.
  • 47
    • 0347424408 scopus 로고    scopus 로고
    • note
    • 2 gave satisfactory results only if the solution was very fresh.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.