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Volumn 46, Issue 48, 2005, Pages 8299-8302

Chiral terpene auxiliaries. Part 1: Highly enantioselective reduction of ketones with borane catalyzed by an oxazaborolidine derived from (-)-β-pinene

Author keywords

1,2 Aminoalcohols; Asymmetric reduction; Chiral oxazaborolidines; Terpenes

Indexed keywords

3 AMINO 6,6 DIMETHYL 2 HYDROXYBICYCLO[3.1.1]HEPTANE; ALCOHOL DERIVATIVE; ALKYL GROUP; BETA PINENE; BORANE DERIVATIVE; HEPTANE DERIVATIVE; KETONE DERIVATIVE; OXAZABOROLIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TERPENE; UNCLASSIFIED DRUG;

EID: 27644528135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.172     Document Type: Article
Times cited : (56)

References (33)
  • 9
    • 27644452052 scopus 로고    scopus 로고
    • note
    • DIP-Chloride is a trademark of the Aldrich Chemical Company.
  • 12
    • 0000777874 scopus 로고    scopus 로고
    • Organic Reactions
    • L.A. Paquette John Wiley New York
    • S. Itsuno L.A. Paquette Organic Reactions Enantioselective Reduction of Ketones Vol. 52 1998 John Wiley New York 395 576
    • (1998) Enantioselective Reduction of Ketones , vol.52 , pp. 395-576
    • Itsuno, S.1
  • 21
    • 27644513559 scopus 로고    scopus 로고
    • note
    • 17NO (155.24): C, 69.63; H, 11.04. Found: C, 69.59; H, 11.21.
  • 22
    • 27644503887 scopus 로고    scopus 로고
    • note
    • 3S (309.43): C, 62.11; H, 7.52. Found: C, 62.11; H, 7.57.
  • 23
    • 27644486479 scopus 로고    scopus 로고
    • note
    • -1; R1 = 0.0432, wR2 = 0.1175; S = 1.092. The relative positions of the tosyl and pinene ring systems is described by the torsion angle values: O2-C2-C3-C4 -101.6(2); C2-C3-N3-S1 -136.17(14); C3-N3-S1-C1′ 61.26(15); N3-S1-C1′-C2′ -107.23(16); the hydrogen bond N3⋯O4 [-x-1/2, y-1/2, -z-1] distance is 3.096 Å.
  • 24
    • 27644537362 scopus 로고    scopus 로고
    • note
    • 3) for >99% ee.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.