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Asymmetric Diels-Alder Cycloadditions with Chiral Carbamoyl Dienophiles (1992)

Defoin, Albert ; Brouillard-Poichet, Agnès ; Streith, Jacques

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 75 (1992), S. 109-123

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Chiral acylnitroso dienophiles 14, which were obtained from L-proline and from D-mandelic acid, reacted with cyclohexa-1,3-diene to give the expected diastereoisomers 15 and 16 (Scheme 2 and Table 1). The d.e. values for these Diels-Alder reactions were moderate; they are related to the molecular stiffness of the dienophiles. The absolute configuration of the major cycloadducts was interpreted in terms of HOMO/LUMO interactions, the approach being ‘endo’ and the acylintroso dienophiles reacting from their s-cis-conformation.

Additional Material: 5 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19920750108

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