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Volumn 129, Issue 10, 2007, Pages 2762-2763

"Super silyl" group for diastereoselective sequential reactions: Access to complex chiral architecture in one pot

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDEHYDE; CYCLOHEXANONE; PIVALALDEHYDE; PIVALIC ACID; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33947286598     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0693542     Document Type: Article
Times cited : (92)

References (25)
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    • Recent examples of one-pot synthesis of stereodefined polyol compounds: (a) Wang, X.; Meng, Q.; Perl, N. R.; Xu, Y.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 12806.
    • Recent examples of one-pot synthesis of stereodefined polyol compounds: (a) Wang, X.; Meng, Q.; Perl, N. R.; Xu, Y.; Leighton, J. L. J. Am. Chem. Soc. 2005, 127, 12806.
  • 9
    • 33947278103 scopus 로고    scopus 로고
    • A highly detailed synthesis of the acetaldehyde super silyl enol ether and its large-scale aldol reaction with pivalaldehyde has been described: Boxer. M. B, Yamamoto, H. Nature Protocols 2006, 1, 2434
    • A highly detailed synthesis of the acetaldehyde super silyl enol ether and its large-scale aldol reaction with pivalaldehyde has been described: Boxer. M. B.; Yamamoto, H. Nature Protocols 2006, 1, 2434.
  • 10
    • 33748241396 scopus 로고    scopus 로고
    • A term coined by Hans Bock: Bock, H.; Meuret, J.; Ruppert, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 414.
    • A term coined by Hans Bock: Bock, H.; Meuret, J.; Ruppert, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 414.
  • 11
    • 0027999819 scopus 로고
    • Hall, N. Science 1994, 266, 32.
    • (1994) Science , vol.266 , pp. 32
    • Hall, N.1
  • 12
    • 0004198491 scopus 로고
    • For sequential and tandem reactions: a, Wiley: New York
    • For sequential and tandem reactions: (a) Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
    • (1992) Tandem Organic Reactions
    • Ho, T.-L.1
  • 14
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    • For acid/base combined systems, see: a
    • For acid/base combined systems, see: (a) Gelman, F.; Blum, J.; Avnir, D. J. Am. Chem. Soc. 2000, 122, 11999.
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 11999
    • Gelman, F.1    Blum, J.2    Avnir, D.3
  • 16
    • 33751385878 scopus 로고    scopus 로고
    • Determined syn via acetonide method of Rychnovsky: Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
    • Determined syn via acetonide method of Rychnovsky: Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
  • 18
    • 0027984321 scopus 로고    scopus 로고
    • The initial aldol reaction proceeds in 91% yield with 77/23 syn/anti selectivity. See Supporting Information for details. This is different from typical β-oxygenated aldehydes (see: Evans, D. A.; Cee, V. J.; Siska, S. J. Tetrahedron Lett. 1994, 35, 8537), but we believe differences arise from the combination of bulky super silyl-enol ether and -cation, which greatly differ from substrates and catalysts in the reference.
    • The initial aldol reaction proceeds in 91% yield with 77/23 syn/anti selectivity. See Supporting Information for details. This is different from typical β-oxygenated aldehydes (see: Evans, D. A.; Cee, V. J.; Siska, S. J. Tetrahedron Lett. 1994, 35, 8537), but we believe differences arise from the combination of bulky super silyl-enol ether and -cation, which greatly differ from substrates and catalysts in the reference.
  • 19
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    • Isolation: Drewes, S. E.; Sehlapelo, B. M.; Horn, M. M.; Scott-Shaw, R.; Sandor, P. Photochemistry 1995, 38, 1427.
    • Isolation: Drewes, S. E.; Sehlapelo, B. M.; Horn, M. M.; Scott-Shaw, R.; Sandor, P. Photochemistry 1995, 38, 1427.
  • 24
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    • ( 13) For calculations comparing energies and structures of models of the super silyl-cation and -enol ether to the TMS-cation and -enol ether, see: Akakura, M.; Boxer, M. B.; Yamamoto, H. Arkivoc 2007, Part x, accepted.
    • ( 13) For calculations comparing energies and structures of models of the super silyl-cation and -enol ether to the TMS-cation and -enol ether, see: Akakura, M.; Boxer, M. B.; Yamamoto, H. Arkivoc 2007, Part x, accepted.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.