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Volumn 63, Issue 3, 1998, Pages 841-859

An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines

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EID: 0000929876     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971706n     Document Type: Article
Times cited : (62)

References (67)
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    • Unpublished results taken from the Ph.D. dissertation of Dino Ferri at the University of Maryland, 1996
    • Unpublished results taken from the Ph.D. dissertation of Dino Ferri at the University of Maryland, 1996.
  • 19
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    • note
    • 2Ph centers and the fact that the active base in each process is most likely different.
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    • Khim, S. K.; Cederstrom, E.; Ferri, D. C.; Mariano, P. S. Tetrahedron 1996, 52, 3195. Kim, S. K.; Wu, X.; Mariano, P. S. Tetrahedron Lett. 1996, 37, 571.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 571
    • Kim, S.K.1    Wu, X.2    Mariano, P.S.3
  • 22
    • 85034470936 scopus 로고    scopus 로고
    • note
    • (a) This stereochemical outcome is consistent with a simple Felkin-Ahn prediction and similar to that observed in other addition reactions of chiral α-amino carbonyl compounds (ref 17b).
  • 24
    • 85034468688 scopus 로고    scopus 로고
    • We have found that CTAN and CAN are about as equally effective in promoting these processes
    • We have found that CTAN and CAN are about as equally effective in promoting these processes.
  • 25
    • 85034470978 scopus 로고    scopus 로고
    • Personal communication from Professor L. E. Overman
    • Personal communication from Professor L. E. Overman.
  • 27
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    • Narasaka (ref 21b) has also demonstrated that α-tin amides undergo oxidation to produce N-acyliminium cations
    • (a) Narasaka (ref 21b) has also demonstrated that α-tin amides undergo oxidation to produce N-acyliminium cations,
  • 36
    • 85034473246 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of 53 contains a small 2.0 Hz H-5,H-6 coupling and a modestly large 5.0 Hz H-4,H-5 coupling both of which are consistent with its existence in a Macromodel-calculated (ca. 2 kcal/ mol) psuedo-diaxial conformation.
  • 37
    • 85034484181 scopus 로고    scopus 로고
    • note
    • Curiously, epimer 65 does not cyclize when treated with CAN. Instead, an MeCN (Ritter-type) trapping product is produced. Similarly, the diacetate of 80 does not undergo oxidative Mannich cyclization. Thus, it appears that other factors can also influence the rates of these processes.
  • 42
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    • Glycoprotein Synthesis and Human Immunodeficiency Viruses
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    • (e) Tyms, A. S.; Taylor, D. L.; Sunkara, P. S.; Kang, M. S. Glycoprotein Synthesis and Human Immunodeficiency Viruses. In Design of Anti-AIDS Drugs; Declerq, E., Ed.; Elsevier: New York, 1990; pp 257-318.
    • (1990) Design of Anti-AIDS Drugs , pp. 257-318
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  • 54
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    • Treatment of the monoacetate of 75 with CAN results in instantaneous O-desilylation
    • Treatment of the monoacetate of 75 with CAN results in instantaneous O-desilylation.
  • 66
    • 85034485174 scopus 로고    scopus 로고
    • For example, hydroquinine 4-chlorobenzoate, hydroquinidine 4-chlorobenzoate, and hydroquinine 1,4-phthalazinediyl diether
    • For example, hydroquinine 4-chlorobenzoate, hydroquinidine 4-chlorobenzoate, and hydroquinine 1,4-phthalazinediyl diether.
  • 67
    • 85034473640 scopus 로고    scopus 로고
    • note
    • When hydroquinine 1,4-phthalazinediyl diether is used in the catalytic hydroxylation reaction of 82, the tetraacetates 85 and 87 are formed in a 2:3 ratio.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.