Facial selectivity in the 4 + 2 reactions of a diene derived from carvone

Morrison, Christopher F.; Vaters, Jamie P.; Miller, David O.; Burnell, D. Jean

doi:10.1039/b516675f

Cited by 4 publications

(2 citation statements)

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“…13 6-(Me,Ts-amino)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone (5i). Following the general procedure D, compound 5i was obtained from tert-butyldimethyl((6-methyl-3-(prop-1-en-2-yl)cyclohexa-1,5dien-1-yl)oxy)silane (0.25 mmol, prepared according to literature procedure 47 ) and N-aminopyridinium salt 1b (0.3 mmol). The crude product was purified by column chromatography to afford 33 mg of compound 5i as colorless oil (yield = 39%, 5 h).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

et al. 2019

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N-Aminopyridinium salts generate nitrogen-centered radicals by means of photoredox catalysis. Herein, we report that they can be trapped by enol equivalents to give α-amino carbonyl compounds in excellent yields. The broad synthetic utility of this method is demonstrated by functionalization of ketones, aldehydes, esters enol equivalents, vinyl ethers, and 1,3-diketones without the need for prior conversion to enol derivatives. The developed method is easily scalable, offers broad substrate scope, high chemoselectivity.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

et al. 2019

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“…Substituent type can be used to predict the facial selectivity (anti-syn) of the Diels-Alder reaction. Generally, as the substituent is on the face opposite to the diene or dienophile, the anti-mode is favored because of its lowest possibility of steric interaction [13]. However, syn addition in Diels-Alder reactions has been observed [14].…”

Section: Introductionmentioning

confidence: 99%

Computational Studies of the Reactivity, Regio-Selectivity and Stereo-Selectivity of Pericyclic Diels-Alder Reactions of Substituted Cyclobutenones

Tia¹

2014

J Theor Comput Sci

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Orbital Phase Environments and Stereoselectivities

Ohwada¹

2009

Orbitals in Chemistry

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Facial selections are reviewed to propose a new theory, orbital phase environment, for stereoselectivities of organic reactions. The orbital phase environment is a generalized idea of the secondary orbital interaction between the non-reacting centers and the unsymmetrization of the orbitals at the reacting centers arising from in-phase and out-of-phase overlapping with those at the neighboring non-reacting sites. In this context, the nucleophilic addition preferentially occurs on the face of the carbonyl functionality opposite to the better electron-donating orbital at the β position. In a similar manner to the carbonyl cases, the preferred reaction faces of olefins in electrophilic addition reactions are opposite to the better electron-donating orbitals at the β positions. The orbital phase environments in Diels-Alder reactions are also reviewed.

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Facial selectivity in the 4 + 2 reactions of a diene derived from carvone

Cited by 4 publications

References 51 publications

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

Computational Studies of the Reactivity, Regio-Selectivity and Stereo-Selectivity of Pericyclic Diels-Alder Reactions of Substituted Cyclobutenones

Orbital Phase Environments and Stereoselectivities

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