About: Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations     Goto   Sponge   NotDistinct   Permalink

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  • 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.
  • 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. (en)
Title
  • Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations
  • Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations (en)
skos:prefLabel
  • Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations
  • Why (1S)-Camphanates Are Excellent Resolving Agents for Helicen-1-ols and Why They Can Be Used to Analyze Absolute Configurations (en)
skos:notation
  • RIV/00216224:14310/00:00036037!RIV10-MSM-14310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • V
http://linked.open...iv/cisloPeriodika
  • 65
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 732770
http://linked.open...ai/riv/idVysledku
  • RIV/00216224:14310/00:00036037
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • helicene; camphanates; resolution (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [4A656517656F]
http://linked.open...i/riv/nazevZdroje
  • Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 2000
http://linked.open...iv/tvurceVysledku
  • Paruch, Kamil
  • Katz, Thomas
  • Lam, Kin-Chung
  • Rheingold, Arnold
  • Liable-Sands, Louise
  • Thongpanchang, Tienthong
issn
  • 0022-3263
number of pages
http://localhost/t...ganizacniJednotka
  • 14310
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