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Volumn 127, Issue 11, 2005, Pages 3964-3972

A theoretical study on the origin of π-facial stereoselectivity in the alkylation of enolates derived from 4-substituted γ-butyrolactones

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; ELECTRON TRANSITIONS; ETHERS; ORGANIC COMPOUNDS;

EID: 15744369238     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044995n     Document Type: Article
Times cited : (22)

References (47)
  • 2
    • 0035978720 scopus 로고    scopus 로고
    • Hyperconjugation is reported to be the origin of torsional strain: Pophristic, V.; Goodman, L. Nature 2001, 411, 565-568.
    • (2001) Nature , vol.411 , pp. 565-568
    • Pophristic, V.1    Goodman, L.2
  • 41
    • 15744393567 scopus 로고    scopus 로고
    • note
    • Even in the presence of a lithium cation, 3-8ax could not be obtained.
  • 42
    • 15744366257 scopus 로고    scopus 로고
    • note
    • 8c
  • 43
    • 15744401837 scopus 로고    scopus 로고
    • note
    • In our hand, 93:7 anti-stereoselectivity was obtained from the reaction of γ-valerolactone with benzyl bromide in THF (LDA, -78 °C). The selectivity is slightly reduced in THF-HMPA (2 equiv) (87:13). Successive dialkylation of γ-valerolactone with methyl iodide and then benzyl bromide in THF (LDA. -78 °C) gave 93:7 anti-selectivitv.
  • 46


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.