Stereoselective [4+2]-Cycloaddition with Chiral Alkenylboranes

Autor:	Kendall N. Houk, Chen Zhou, Dongshun Ni, M. Kevin Brown, Hong Zhang, Brittany P. Witherspoon
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Stereospecificity chemistry 010405 organic chemistry Stereochemistry Stereoselectivity General Chemistry Counterion 010402 general chemistry 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences
Zdroj:	Angewandte Chemie (International ed. in English). 59(28)
ISSN:	1521-3773
Popis:	A method for the stereoselective [4+2]-cycloaddition of alkenylboranes and dienes is presented. This transformation was accomplished through the introduction of a new strategy that involves the use of chiral N-protonated alkenyl oxazaborolidines as dieneophiles. The reaction leads to the formation of products that can be readily derivatized to more complex structural motifs through stereospecific transformations of the C-B bond such as oxidation and homologation. Detailed computation evaluation of the reaction has uncovered a surprising role of the counterion on stereoselectivity.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6114dcd0c2b14ab18965d4a532aa07f3 https://pubmed.ncbi.nlm.nih.gov/32390259 Zobrazit plný text záznamu Plný text