THONGPANCHANG, Tienthong, Kamil PARUCH, Thomas KATZ, Arnold RHEINGOLD, Kin-Chung LAM and Louise LIABLE-SANDS. Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations. Journal of Organic Chemistry. 2000, vol. 2000, No 65, p. 1850-1856. ISSN 0022-3263.
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Basic information
Original name Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations
Name in Czech Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations
Authors THONGPANCHANG, Tienthong (840 United States of America), Kamil PARUCH (203 Czech Republic, guarantor), Thomas KATZ (840 United States of America), Arnold RHEINGOLD (840 United States of America), Kin-Chung LAM (840 United States of America) and Louise LIABLE-SANDS (840 United States of America).
Edition Journal of Organic Chemistry, 2000, 0022-3263.
Other information
Original language English
Type of outcome Article in a journal
Field of Study 10401 Organic chemistry
Country of publisher United States of America
Confidentiality degree is not subject to a state or trade secret
Impact factor Impact factor: 3.689
RIV identification code RIV/00216224:14310/00:00036037
Organization unit Faculty of Science
Keywords (in Czech) helicene; camphanates; resolution
Keywords in English helicene; camphanates; resolution
Tags camphanates, helicene, RESOLUTION
Changed by Changed by: doc. Mgr. Kamil Paruch, Ph.D., učo 108413. Changed: 25/6/2009 15:27.
Abstract
The questions considered in this paper are why, as agents for resolving helicenols, camphanate esters are particularly effective, and why, in all 19 examples studied, when the (1S)-camphanates of (P)- and (M)-helicen-1-ols are chromatographed on silica gel, the former has the lower Rf. Models are proposed for the favored conformations of the esters, and to support the models, evidence is provided from five X-ray diffraction analyses and four ROESY analyses supplemented by mol. mechanics calcns. The essential discovery is that, presumably to avoid a steric interaction between a Me on the camphanate's bridge and the helicene skeleton, the O:CCO conformation is anti-periplanar in (M)-helicenol camphanates and syn-periplanar in (P)-helicenol camphanates. In the former, the lactone carbonyl points toward the helicene ring system, and in the latter, it points away.
Abstract (in Czech)
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