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Volumn 65, Issue 36, 2009, Pages 7516-7522

Al Lewis acid-catalyzed regiodivergent 1,2-rearrangement of α-siloxy aldehydes: scope and mechanism

Author keywords

Aluminum; Lewis acids; Rearrangement; Regioselectivity; Synthetic methods

Indexed keywords

ALDEHYDE; ALPHA SILOXY ALDEHYDE DERIVATIVE; ALPHA SILOXY KETONE DERIVATIVE; ALUMINUM; KETONE; LEWIS ACID; SOLVENT; UNCLASSIFIED DRUG;

EID: 67949086864     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.126     Document Type: Article
Times cited : (9)

References (36)
  • 4
    • 0000688199 scopus 로고
    • For review:. Trost B.M., and Fleming I. (Eds), Pergamon, New York, NY Chapter 3
    • For review:. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York, NY 705 Chapter 3
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 705
  • 5
    • 67949098478 scopus 로고    scopus 로고
    • For reviews of atom economy, see
    • For reviews of atom economy, see:
  • 9
    • 67949090649 scopus 로고    scopus 로고
    • Pinacol rearrangement
    • Pinacol rearrangement:
  • 13
    • 67949092171 scopus 로고    scopus 로고
    • Wagner-Meerwein rearrangement
    • Wagner-Meerwein rearrangement:
  • 32
    • 0025355715 scopus 로고
    • For a report describing the difference in Lewis acidity of MAD and MABR, see:
    • For a report describing the difference in Lewis acidity of MAD and MABR, see:. Nonoshita K., Banno H., Maruoka K., and Yamamoto H. J. Am. Chem. Soc. 112 (1990) 316
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 316
    • Nonoshita, K.1    Banno, H.2    Maruoka, K.3    Yamamoto, H.4
  • 33
    • 67949101576 scopus 로고    scopus 로고
    • note
    • The reaction under the influence of 5b underwent the non-regioselective migration of [TBS]-1b, affording 1:6 ratio of alkyl-migrated product 2 and phenyl-migrated one 3. The distributions of silyl groups were also observed in this case.
  • 34
    • 33646200367 scopus 로고    scopus 로고
    • In Mukaiyama aldol reaction, the silyl enol ether can become the catalyst for the next catalytic cycle:
    • In Mukaiyama aldol reaction, the silyl enol ether can become the catalyst for the next catalytic cycle:. Hiraiwa Y., Ishihara K., and Yamamoto H. Eur. J. Org. Chem. (2006) 1837
    • (2006) Eur. J. Org. Chem. , pp. 1837
    • Hiraiwa, Y.1    Ishihara, K.2    Yamamoto, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.