75506-74-0Relevant articles and documents
An Improved Preparation of Δ8,9-Octal-1-one
Abbott, Richard E.,Spencer, Thomas A.
, p. 5398 - 5399 (1980)
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(Poly)cationic λ3-Iodane-Mediated Oxidative Ring Expansion of Secondary Alcohols
Walters, Jennifer C.,Tierno, Anthony F.,Dubin, Aimee H.,Wengryniuk, Sarah E.
, p. 1460 - 1464 (2018/04/06)
Herein, a simplified approach to the synthesis of medium-ring ethers through the electrophilic activation of secondary alcohols with (poly)cationic λ3-iodanes (N-HVIs) is reported. Excellent levels of selectivity are achieved for C–O bond migration over established α-elimination pathways, enabled by the unique reactivity of a novel 2-OMe-pyridine-ligated N-HVI. The resulting hexafluoroisopropanol (HFIP) acetals are readily derivatized with a range of nucleophiles, providing a versatile functional handle for subsequent manipulations. The utility of this methodology for late-stage natural product derivatization was also demonstrated, providing a new tool for diversity-oriented synthesis and complexity-to-diversity (CTD) efforts. Preliminary mechanistic investigations reveal a strong effect of alcohol conformation on the reactive pathway, thus providing a predictive power in the application of this approach to complex molecule synthesis.
2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds
Ramon, Diego J.,Yus, Miguel
, p. 3763 - 3766 (2007/10/02)
2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at -78°C. The reaction of these masked bishomoenolates with different electrophiles yie
