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Volumn 15, Issue 14, 2009, Pages 3363-3366

Stereoselective Se2′ protonation of α- hydroxyallylsilanes mediated by a brook rearrangement

Author keywords

Asymmetric synthesis; Carbanions; Chixality; Enantioselectivity; Silicates

Indexed keywords

ALKOXIDE; ALLYLSILANES; ASYMMETRIC SYNTHESIS; BROOK REARRANGEMENTS; CARBANIONS; CHIXALITY; GAIN INFORMATIONS; INVERSION BARRIERS; RE ARRANGEMENTS; STEREO-SELECTIVE; STEREOCHEMICAL PATHWAYS;

EID: 63749085376     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802499     Document Type: Article
Times cited : (12)

References (34)
  • 5
    • 0035835953 scopus 로고    scopus 로고
    • for the use of the Brook rearrangement in tandem bond formation strategies, see; d W. H. Moser. Tetrahedron 2001, 57, 2065-2084. Also, see:
    • for the use of the Brook rearrangement in tandem bond formation strategies, see; d) W. H. Moser. Tetrahedron 2001, 57, 2065-2084. Also, see:
  • 11
    • 23844544536 scopus 로고    scopus 로고
    • We have discussed the stereochemical pathway of reactions involving allylsilicates and related system; a K. Tanaka. H. Masu, K. Yamaguchi, K. Takeda, Tetrahedron Lett. 2005, 46, 6429-6432;
    • We have discussed the stereochemical pathway of reactions involving allylsilicates and related system; a) K. Tanaka. H. Masu, K. Yamaguchi, K. Takeda, Tetrahedron Lett. 2005, 46, 6429-6432;
  • 17
    • 63749122110 scopus 로고    scopus 로고
    • We have sometimes observed that the rate of Brook rearrangement in Et2O is much slower than that in THF
    • 2O is much slower than that in THF.
  • 20
    • 63749084802 scopus 로고    scopus 로고
    • We have recently found that the mode of a base-induced ring-opening of epoxysilanes can change depending on solvents, which will be reported in future publication
    • We have recently found that the mode of a base-induced ring-opening of epoxysilanes can change depending on solvents, which will be reported in future publication.
  • 23
    • 63749093423 scopus 로고    scopus 로고
    • Calculations were performed on the Spartan 06 and Conflex programs: Spartan 06 (Ver. 1.0.1 for Mac, Wavefunction. Inc, Irvine. CA: Conflex (Ver. 6.2 for Mac, H. Goto. K. Ohta, T. Kamakura, S. Obata. Nakayama, T. Matsumoto. E. Osawa. Conflex Corporation. Tokyo Japan, 2004
    • Calculations were performed on the Spartan 06 and Conflex programs: Spartan 06 (Ver. 1.0.1 for Mac). Wavefunction. Inc, Irvine. CA: Conflex (Ver. 6.2 for Mac). H. Goto. K. Ohta, T. Kamakura, S. Obata. Nakayama, T. Matsumoto. E. Osawa. Conflex Corporation. Tokyo (Japan), 2004.
  • 25
    • 0036135888 scopus 로고    scopus 로고
    • For α-nitrile carbanions, see: a
    • For α-nitrile carbanions, see: a) F. F. Fleming, B. C. Shook. Tetrahedron 2002, 58, 1-23;
    • (2002) Tetrahedron , vol.58 , pp. 1-23
    • Fleming, F.F.1    Shook, B.C.2
  • 34
    • 63749121002 scopus 로고    scopus 로고
    • We believe that the effect of the carbamoyloxy group is not so large because the corresponding O-TBS derivatives afforded the protonated products in ca. 40% ee. Details will be reported in a full paper. Also, see: ref, 1
    • We believe that the effect of the carbamoyloxy group is not so large because the corresponding O-TBS derivatives afforded the protonated products in ca. 40% ee. Details will be reported in a full paper. Also, see: ref. [1].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.