Allylic Stereocontrol of the Intramolecular Diels-Alder Reaction

Autor:	Peter Turner, Michael S. Sherburn, Alison J. Edwards, Michael J. Lilly, Michael N. Paddon-Row, Natalie A. Miller, Anthony C. Willis
Rok vydání:	2005
Předmět:	Substitution reaction Allylic rearrangement Molecular Structure Computers Stereochemistry Chemistry Organic Chemistry Malates Stereoisomerism Ascorbic Acid General Chemistry Catalysis Cycloaddition Stereocenter Cyclo addition Models Chemical Intramolecular force Lactic Acid Diels–Alder reaction
Zdroj:	Chemistry - A European Journal. 11:2525-2536
ISSN:	1521-3765 0947-6539
DOI:	10.1002/chem.200401215
Popis:	The stereochemical outcome phile. The stereochemical outcomes of structures. New insights into the conof the intramolecular Diels-Alder reac- these reactions are explained by refer- formational preferences of allylic alcotion of ester-linked 1,3,8-nonatrienes ence to B3LYP/6-31G(d) transition hol derivatives are reported, results can be controlled by substituents about which allow an explanation of the difa stereogenic center attached to Cl. fering levels of π-diastereofacial selecThe scope and limitations of this ap- tivity and cis/trans (i.e. endo/exo) selecproach have been investigated, with tivity from the reaction. variation in substrate structure about the allylic stereocenter and the dieno.
Databáze:	OpenAIRE
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