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Volumn 1, Issue 7, 1999, Pages 1115-1118

Methyllithium-promoted Wittig rearrangements of α-alkoxysilanes

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; LITHIUM; SILANE DERIVATIVE;

EID: 0033533657     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990912+     Document Type: Article
Times cited : (19)

References (48)
  • 3
    • 0000535071 scopus 로고
    • Pattenden, G., Ed.; Pergamon: London
    • (c) Marshall, J. A. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon: London, 1991; Vol. 3, pp 975-1014.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 975-1014
    • Marshall, J.A.1
  • 4
    • 0000080952 scopus 로고
    • Pattenden, G., Ed.; Pergamon: London
    • (d) Bruckner, R. In Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon: London, 1991; Vol. 6, pp 873-908.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 873-908
    • Bruckner, R.1
  • 6
    • 0003662390 scopus 로고    scopus 로고
    • Blackie Academic & Professional: New York
    • (a) Chemistry of Tin; Smith, P. J., Ed.; Blackie Academic & Professional: New York, 1998.
    • (1998) Chemistry of Tin
    • Smith, P.J.1
  • 25
    • 0002092942 scopus 로고
    • For examples of the directed deprotonation and rearrangement of vinylogous α-alkoxysilanes, see: (a) Mikami, K.; Kishi, N.; Nakai, T. Chem. Lett. 1989, 1683-1686.
    • (1989) Chem. Lett. , pp. 1683-1686
    • Mikami, K.1    Kishi, N.2    Nakai, T.3
  • 27
    • 0041647929 scopus 로고
    • The [1,2]-Wittig rearrangement of [(aryloxy)methyl]silanes has been initiated by deprotonation and affords α-silylbenzyl alcohols. See: Eisch, J. J.; Galle, J. E.; Piotrowski, A.; Tsai, M.-R. J. Org. Chem. 1982, 47, 5051-5056.
    • (1982) J. Org. Chem. , vol.47 , pp. 5051-5056
    • Eisch, J.J.1    Galle, J.E.2    Piotrowski, A.3    Tsai, M.-R.4
  • 28
    • 85034128309 scopus 로고    scopus 로고
    • note
    • The starting α-alkoxysilanes were prepared by reaction of the corresponding α-silyl alcohols with allyl or benzyl trichloroimidates in the presence of catalytic quantities of TMSOTf. For details, see the preceding Letter this issue (see ref 8).
  • 29
    • 0002049382 scopus 로고
    • [2,3]-Wittig rearrangement of the dessilyl analogue of 1 proceeds with similar (2:1) preference for the erythro product (Schöllkopf, U.; Fellenberger, K.; Rizk, M. Liebigs Ann. Chem. 1970, 734, 106-115).
    • (1970) Liebigs Ann. Chem. , vol.734 , pp. 106-115
    • Schöllkopf, U.1    Fellenberger, K.2    Rizk, M.3
  • 30
    • 85034122219 scopus 로고    scopus 로고
    • note
    • The same reaction sequence applied to 2b provided analogous results.
  • 31
    • 85034124301 scopus 로고    scopus 로고
    • Reference 7b
    • (a) Reference 7b.
  • 35
    • 85034135385 scopus 로고    scopus 로고
    • note
    • While the retro-Brook sequence only gave 21% of the desired α-hydroxysilane, 67% of the silyl ether was also recovered. Presumably this material could be recycled; however, no attempt to optimize the process was made.
  • 37
    • 85034126585 scopus 로고    scopus 로고
    • note
    • 2O at room temperature over 16 h. See Supporting Information for more details.
  • 40
    • 0011972850 scopus 로고
    • Although we have no direct evidence of any O-silyl products, the 1,3-silyl migration probably takes place via Brook rearrangement (ref 11) of 26 followed by rearrangement of the resulting homoenolate. For similar examples, see: (a) Kuwajima, I. J. Organomet. Chem. 1985, 285, 137-148.
    • (1985) J. Organomet. Chem. , vol.285 , pp. 137-148
    • Kuwajima, I.1
  • 48
    • 0001050524 scopus 로고
    • and references therein
    • (c) Hsiao, C. N.; Shechter, H. J. Org. Chem. 1988, 53, 2688-2699 and references therein.
    • (1988) J. Org. Chem. , vol.53 , pp. 2688-2699
    • Hsiao, C.N.1    Shechter, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.