About: Stereoretentive O-to-C Rearrangement of Vinyl Acetals: Solvent Cage Effectsas a Stereocontrol Element

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Attributs	Valeurs
type	work Article
Is Part Of	http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/w
Subject	Communication
Title	Stereoretentive O-to-C Rearrangement of Vinyl Acetals: Solvent Cage Effectsas a Stereocontrol Element
has manifestation of work	http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/m/web http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/m/print
related by	http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/authorship/1 http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/authorship/2 http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/authorship/3 http://hub.abes.fr/acs/periodical/jacsat/2002/volume_124/issue_33/101021ja026972j/authorship/4
Author	Rovis Tomislav Reynolds Nathan T. Zhang Yongda Manju Kavita
Abstract	The Lewis acid-mediated rearrangement of chiral vinyl acetals may be induced to provide the product of stereoretention using Me3Al and BF3·OEt2 in concert. The selectivities obtained in this reaction (86:14 to 96:4) are complementary to that observed when relying on oxocarbenium facial bias to control the newly formed stereocenter. Evidence is presented that this reaction occurs by tight ion-pair binding in the solvent cage. The relay of C−O bond stereochemistry to a C−C bond stereocenter via ionic intermediates is an addition to similar established methods such as the Claisen rearrangement.
article type	rapid-communication
is part of this journal	Journal of the American Chemical Society

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