Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Easy access to 2-arylpyrrolidines

March 13, 2006 | A version of this story appeared in Volume 84, Issue 11

The most convergent and reliable method yet for constructing 2-arylpyrrolidines-a structural motif found in many biologically active compounds and chiral auxiliaries used in asymmetric catalysis-has been developed by process chemists at Merck Research Laboratories in Rahway, N.J (J. Am. Chem. Soc., published online March 1, dx.doi.org/10.1021/ja0605265). Kevin R. Campos and coworkers report a one-pot, enantioselective process that can be used to prepare a broad range of functionalized 2-aryl-N-Boc-pyrrolidines from N-Boc-pyrrolidine with high enantioselectivity (shown; Boc = tert-butoxycarbonyl, Ar = aryl). The methodology relies on the asymmetric deprotonation of N-Boc-pyrrolidine with sec-butyllithium and the chiral diamine (–)-sparteine, followed by transmetalation with zinc. The 2-pyrrolidinozinc reagent generated is then coupled to functionalized aryl halides at room temperature using a palladium catalyst. Preliminary unpublished results suggest that the arylation reaction will be applicable to other substrates as well, Campos notes.

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.