Efavirenz: spot the stereochemistry flaw

Single question

Penultimate step in the efavirenz process: asymmetric alkynyl-zinc addition of cyclopropylacetylide to the 2-trifluoroacetyl-4-chloroaniline ketone. Catalyst class and conditions match. Check the absolute configuration on the new quaternary carbon.

Asymmetric alkynyl-zinc addition to trifluoromethyl ketones

(R) vs (S) at the efavirenz quaternary carbinol

Reading absolute configuration on quaternary stereocenters

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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