Chelation-control in nucleophilic addition to Cr(CO)3-complexed aryl aldehydes

Suresh Kumar Tipparaju; Vedavati G. Puranik; Amitabha Sarkar

doi:10.1039/B301426F

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Chelation-control in nucleophilic addition to Cr(CO)₃-complexed aryl aldehydes†

Suresh Kumar Tipparaju,^a Vedavati G. Puranik^b and Amitabha Sarkar ‡*^a

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* Corresponding authors

^a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India

^b Physical Chemistry Division, National Chemical Laboratory, Pune 411 008, India

Abstract

One or more methoxy groups on the benzylic carbon at the ortho-position of tricarbonylchromium-complexed aryl aldehydes (2, 3 or 4) permit chelation-controlled addition of nucleophiles to the carbonyl function in the presence of Lewis acids. In the absence of a Lewis acid additive, a complementary set of diastereomeric products are obtained.

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Article information

DOI: https://doi.org/10.1039/B301426F
Article type: Paper
Submitted: 06 Feb 2003
Accepted: 26 Mar 2003
First published: 11 Apr 2003

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Org. Biomol. Chem., 2003,1, 1720-1725

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Chelation-control in nucleophilic addition to Cr(CO)₃-complexed aryl aldehydes

S. Kumar Tipparaju, V. G. Puranik and A. Sarkar, Org. Biomol. Chem., 2003, 1, 1720 DOI: 10.1039/B301426F

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Organic & Biomolecular Chemistry