메뉴 건너뛰기




Volumn 36, Issue 42, 1995, Pages 7615-7618

Regio- and stereocontrolled syntheses of cyclic chiral cis-amino alcohols from 1,2-diols or epoxides

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZOSUBERANE DERIVATIVE; INDAN DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0028787044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)01583-4     Document Type: Article
Times cited : (65)

References (32)
  • 10
    • 0002578608 scopus 로고
    • Asymmetric Catalytic Epoxidation of Unfunctionalized Olefins
    • For the preparation of chiral styrene oxide derivatives via asymmetric metal catalysis, see, and references cited therein, I. Ojima, VCH, Oxford, U.K., and references cited therein
    • (1994) Catalytic Asymmetric Synthesis , pp. 159
    • Jacobsen1
  • 12
    • 0001432359 scopus 로고
    • For the preparation of chiral styrene oxide derivatives via asymmetric metal catalysis, see, For the preparation of tetralin oxide in 98% ee, see
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 12129
    • Jacobsen1    Larrow2
  • 19
    • 84915372824 scopus 로고    scopus 로고
    • For the preparation of indene oxide in >99% ee via enzymatic resolution, see: Zhang, J.; Chartrain, M.; Greasham, R.; Senanayake, C. H. manuscript in preparation.
  • 23
    • 84915372823 scopus 로고    scopus 로고
    • Indene has been converted to cis-indene diol in 〉99% ee with a dioxygenase, Greasham R. unpublished results
  • 26
    • 84915372821 scopus 로고    scopus 로고
    • In the case of the 5,5-ring system the trans-closure is conformationally difficult
  • 27
    • 84915372820 scopus 로고    scopus 로고
    • These results suggest that the tetralin oxide first generates the C-1 carbenium ion which is trapped by nucleophiles present in the media. In the case of methanesulfonic acid, the C-1 carbenium ion 4b is trapped by acetonitrile or methanesulfonic acid to provide the C-1 nitrilium intermediate 5b or C-1 mesylate 7b, respectively. The nitrilium intermediates generate the corresponding cis- and trans-oxazoline 7b and amido alcohol 8.
  • 28
    • 84915372819 scopus 로고    scopus 로고
    • Unlike the tetralin oxide, there is no trans-amido alcohol 8 observed in this reaction.
  • 29
    • 84915372818 scopus 로고    scopus 로고
    • 3NO) and Mn-S,S-salen catalyst The olefin was added at 0 °C. The reaction progress was followed by HPLC. The absolute stereochemistry of epoxide 2 was established as in reference 5c.
  • 30
    • 84915372817 scopus 로고    scopus 로고
    • 4 at 0 °C.
  • 31
    • 84915372816 scopus 로고    scopus 로고
    • 13C NOEDS), 2-D (COSY, HETCOR) etc. and comparing the cis-and trans-methyl oxazolines (6) and cis- and trans- amino alcohols 1. The absolute stereochemistry of cis-amino alcohol 1 was based on the known C-2 absolute stereochemistry of epoxide 2 or diol 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.