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Volumn , Issue 14, 2005, Pages 1906-1908

Erratum: Novel chemoselective tosylation of the alcoholic hydroxyl group of syn-α,β-disubstituted β-hydroxy carboxylic acids (Chemical Communications (2005) (DOI: 10.1039/b416383d);Novel chemoselective tosylation of the alcoholic hydroxyl group of syn-α,β-disubstituted β-hydroxy carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; BETA HYDROXYCARBOXYLIC ACID DERIVATIVE; BETA TOSYLOXY ACID; CARBOXYLIC ACID DERIVATIVE; HYDROXYL GROUP; LACTONE DERIVATIVE; LITHIUM DERIVATIVE; METHYLLITHIUM; UNCLASSIFIED DRUG;

EID: 17444368622     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b416383d     Document Type: Erratum
Times cited : (12)

References (39)
  • 1
    • 0013583352 scopus 로고    scopus 로고
    • (a) α-Substituted-N-benzoyl-serine (with highly hindered carboxylic but non-hindered alcoholic OH) is the only exception: A. Olma, Pol. J. Chem., 1996, 70, 1442-1447;
    • (1996) Pol. J. Chem. , vol.70 , pp. 1442-1447
    • Olma, A.1
  • 16
  • 21
    • 0024294399 scopus 로고
    • See, e.g.: (a) D. A. Evans, Science, 1988, 240, 420-426;
    • (1988) Science , vol.240 , pp. 420-426
    • Evans, D.A.1
  • 22
    • 0035830561 scopus 로고    scopus 로고
    • (b) M. T. Crimmins, B. W. King, E. A. Tabet and K. Chaudhary, J. Org. Chem., 2001, 66, 894-902. Note that the absolute configurations of the newly formed chiral centers in the aldols are predictable in almost all cases and a great many different substituents at the α and β carbons have been reported in the literature over the last few decades.
    • (2001) J. Org. Chem. , vol.66 , pp. 894-902
    • Crimmins, M.T.1    King, B.W.2    Tabet, E.A.3    Chaudhary, K.4
  • 23
    • 0037155499 scopus 로고    scopus 로고
    • For example, the Mitsunobu reaction, which is well-known for configuration inversion at the hydroxyl carbon in the synthesis of lactones, does not always lead to inversion. See: (a) C. Ahn and P. DeShong, J. Org. Chem., 2002, 67, 1754-1759. Note also that the Mitsunobu reaction is only rarely applicable to the synthesis of β-lactones (β-unsubstituted/unhindered at the alcoholic OH).
    • (2002) J. Org. Chem. , vol.67 , pp. 1754-1759
    • Ahn, C.1    DeShong, P.2
  • 27
    • 0038512229 scopus 로고    scopus 로고
    • (b) M. Taniguchi, K.-I. Suzumura, K. Nagai, T. Kawasaki, T. Saito, J. Takasaki, K.-I. Suzuki, S. Fujita and S.-I. Tsukamoto, Tetrahedron, 2003, 59, 4533-4538. However, such conditions completely failed to give any 2 when applied to 1 (presumably because the OTs, as in our substrates, is a much better leaving group than OMe or OBn, as in the literature cases, and thus more liable to various side reactions under the literature conditions).
    • (2003) Tetrahedron , vol.59 , pp. 4533-4538
    • Taniguchi, M.1    Suzumura, K.-I.2    Nagai, K.3    Kawasaki, T.4    Saito, T.5    Takasaki, J.6    Suzuki, K.-I.7    Fujita, S.8    Tsukamoto, S.-I.9
  • 32
    • 0033591141 scopus 로고    scopus 로고
    • For pre-1999 reports on the synthesis of β-lactones in general, see an excellent review: (a) H. W. Yang and D. Romo, Tetrahedron, 1999, 55, 6403-6434.
    • (1999) Tetrahedron , vol.55 , pp. 6403-6434
    • Yang, H.W.1    Romo, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.