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Volumn 45, Issue 48, 2006, Pages 8217-8220

Polyol synthesis through hydrocarbon oxidation: De novo synthesis of L-galactose

Author keywords

Allylic oxidation; C H activation; Carbohydrates; Enantioselectivity; Polyols

Indexed keywords

ALCOHOLS; HYDROCARBONS; OXIDATION; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

EID: 33845745902     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603321     Document Type: Article
Times cited : (68)

References (46)
  • 11
    • 0037015432 scopus 로고    scopus 로고
    • For example, see
    • For example, see: a) L. Jiang, S. D. Burke, Org. Lett. 2002, 4, 3411;
    • (2002) Org. Lett. , vol.4 , pp. 3411
    • Jiang, L.1    Burke, S.D.2
  • 24
    • 0025601763 scopus 로고
    • For syntheses of chiral (E)-2-buten-1,4-diols with good to moderate enantioselectivities from allylation with chiral (E)-γ- (dimethylphenylsilyl)allylboronate reagents followed by epoxidation/Petersen elimination, see: a) W. R. Roush, P. T. Grover, Tetrahedron Lett. 1990, 31, 7567;
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7567
    • Roush, W.R.1    Grover, P.T.2
  • 26
    • 33644641498 scopus 로고    scopus 로고
    • For representative asymmetric allylation reactions, see: a) G. Xia. H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 2554;
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 2554
    • Xia, G.1    Yamamoto, H.2
  • 34
    • 33845800907 scopus 로고    scopus 로고
    • PhD thesis, Harvard University (USA)
    • b) C. P. Stevenson, PhD thesis, Harvard University (USA) 2005;
    • (2005)
    • Stevenson, C.P.1
  • 39
    • 33845770816 scopus 로고    scopus 로고
    • note
    • III]OAc (2 mol %) to give the desired chiral epoxyketal in 50 % overall yield (95 % ee). Lower yields may be attributed to epoxide opening by MeOH during the ketalization step with higher catalyst loadings of the monomeric catalyst. See the Supporting Information for details.
  • 40
    • 33845796600 scopus 로고    scopus 로고
    • note
    • The diastereomer which corresponds to racemization of the allylic center was independently synthesized and was not detected in the HPLC analysis of the products (see the Supporting Information for details).
  • 43
    • 30744454015 scopus 로고    scopus 로고
    • (see the Supporting Information for details)
    • The silyl groups were removed and (-)-11 was peracetylated to give 1,2,3,6-O-tetraacetyl-4-O-benzyl-L-galactopyranose, the spectroscopic data of which was found to correspond to those reported for the known compound (see the Supporting Information for details): L. Ermolenko, N. A. Sasaki, J. Org. Chem. 2006, 71, 693.
    • (2006) J. Org. Chem. , vol.71 , pp. 693
    • Ermolenko, L.1    Sasaki, N.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.