Organic Chemistry

An asymmetric route to amino alcohols

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Science  01 Jan 2016:
Vol. 351, Issue 6268, pp. 38-39
DOI: 10.1126/science.351.6268.38-g

Amines and alcohols are among the most common and versatile functional groups in organic chemistry. The nitroso variant of the Diels-Alder reaction is a convenient means of introducing both to the same molecule. Both ends of the N=O group form a bridge between the outer carbons in a C=C-C=C diene motif, after which the lingering N-O bond can be severed. Maji and Yamamoto present a highly selective asymmetric variant of this reaction, catalyzed by a copper complex bearing a chiral diphosphine ligand. The reaction couples a range of cyclic dienes with nitroso pyrimidines and pyridazines.

J. Am. Chem. Soc. 10.1021/jacs.5b11273 (2015).

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