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Volumn 2, Issue 17, 2000, Pages 2659-2661

Use of optically active cyclic N,N-dialkyl aminals in asymmetric induction

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE;

EID: 0034710469     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0001517     Document Type: Article
Times cited : (122)

References (30)
  • 1
    • 0002032726 scopus 로고
    • For a good review, see: Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
    • (1989) Chem. Rev. , vol.89 , pp. 1581
    • Whitesell, J.K.1
  • 2
    • 24544448140 scopus 로고
    • Université Pierre et Marie Curie, Paris
    • (a) For example, Alexakis observed that the cyclization of the anion 1 (R = Me) gave a product with a de of 52% in 29% isolated yield. A. Alexakis, personal communication. See also: Nirouël, V. Diplôme d'Etude Approfondi, Université Pierre et Marie Curie, Paris, 1993. For other examples, see:
    • (1993) Diplôme d'Etude Approfondi
    • Nirouël, V.1
  • 7
    • 0040827748 scopus 로고
    • Ph.D. Thesis, Université Pierre et Marie Curie, Paris, 1995. Londez, A. Diplôme d'Etude Approfondi, Université Pierre et Marie Curie, Paris
    • The Alexakis group has been able to prepare substituted aminals of ketones (but not enones) under fairly harsh conditions. A. Alexakis, personal communication. See also: Tranchier, J.-P. Ph.D. Thesis, Université Pierre et Marie Curie, Paris, 1995. Londez, A. Diplôme d'Etude Approfondi, Université Pierre et Marie Curie, Paris, 1995.
    • (1995)
    • Tranchier, J.-P.1
  • 13
    • 0001798476 scopus 로고    scopus 로고
    • Stephenson, G. R., Ed., Chapman and Hall: London; Chapter 5
    • (f) For a good review, see: Alexakis, A.; Mangeney. P. In Advanced Asymmetric Synthesis; Stephenson, G. R., Ed., Chapman and Hall: London, 1996; Chapter 5, pp 93-110.
    • (1996) Advanced Asymmetric Synthesis , pp. 93-110
    • Alexakis, A.1    Mangeney, P.2
  • 21
    • 0039641275 scopus 로고    scopus 로고
    • note
    • We thank Dr. Saeed Khan for his assistance in obtaining this crystal structure.
  • 22
    • 0040233128 scopus 로고    scopus 로고
    • note
    • In one experiment when a larger amount of potassium tert-butoxide was used, the 1H pyrazoline i was isolated in essentially quantitative yield. This compound is presumably formed by isomerization of the initially formed pyrazoline 16. (formula presented)
  • 23
    • 0039049212 scopus 로고    scopus 로고
    • note
    • Although the ratio of products is dependent on the relative energies of the transition states leading to them, one can often estimate the differences by examining the energies of the products. Calculations (PM3) of close models (with hydrogen in place of benzyl) indicate that the two products 18 and 19 are essentially equivalent in energy (19-H is favored by 0.28 kcal/mol over 18-H) while the two pyrazolines (16 and epi-16. the other cis diastereomer) are very different in energy with 16 being favored by 2.6 kcal/mol.
  • 27
    • 1642399445 scopus 로고    scopus 로고
    • The octant rule
    • Nakanishi, K., Berova, N., Woody, R. W., Eds.; Wiley-Interscience: New York; Chapter 10
    • (b) Lightner, D. A. The Octant Rule. Circular Dichroism: Principles and Applications, 2nd ed.; Nakanishi, K., Berova, N., Woody, R. W., Eds.; Wiley-Interscience: New York, 2000; Chapter 10.
    • (2000) Circular Dichroism: Principles and Applications, 2nd Ed.
    • Lightner, D.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.