메뉴 건너뛰기




Volumn , Issue 12, 1999, Pages 1647-1656

Dispiroketals in synthesis. Part 25.1 Further reactions of dispiroketal protected glycolate to afford optically active 1,2,3,4-tetraols

Author keywords

[No Author keywords available]

Indexed keywords


EID: 0002468787     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900951e     Document Type: Article
Times cited : (22)

References (36)
  • 5
    • 0015245199 scopus 로고    scopus 로고
    • 1971, 172, 495; R. E. Moore and G. Bartoiini, J. Am. Chem. Soc., 1981,103,2491.
    • P. J. Scheuer and R. E. Moore, Science, 1971, 172, 495; R. E. Moore and G. Bartoiini, J. Am. Chem. Soc., 1981,103,2491.
    • Science
    • Scheuer, P.J.1    Moore, R.E.2
  • 18
    • 33746466428 scopus 로고    scopus 로고
    • In referring to diastereoisomers obtained from reaction of nonchiral starting materials, their racemic nature is assumed and only one enantiomeric form is depicted in their formulae.
    • In referring to diastereoisomers obtained from reaction of nonchiral starting materials, their racemic nature is assumed and only one enantiomeric form is depicted in their formulae.
  • 24
    • 33746394934 scopus 로고    scopus 로고
    • During further studies of these aldol reactions, it was found that replacing DMPU by HMPA enhanced the nucleophilicity of the enolate of 18 (antipode of 4). Under these conditions it was possible (Figure Presented) Reagents and conditions: i, Pr"2NH, Bu"Li, THF-HMPA (3:1 mixture), -78 °C, 30 min then pivaldehyde at -78 °C, 30 min. to carry out the reaction with pivalaldehyde and a single compound was isolated in 58% yield. The stereochemistry of this compound was not formally established but was predicted to be erythro according to the transition states shown in Scheme 2.
    • During further studies of these aldol reactions, it was found that replacing DMPU by HMPA enhanced the nucleophilicity of the enolate of 18 (antipode of 4). Under these conditions it was possible (Figure Presented) Reagents and conditions: i, Pr"2NH, Bu"Li, THF-HMPA (3:1 mixture), -78 °C, 30 min then pivaldehyde at -78 °C, 30 min. to carry out the reaction with pivalaldehyde and a single compound was isolated in 58% yield. The stereochemistry of this compound was not formally established but was predicted to be erythro according to the transition states shown in Scheme 2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.