Diastereodivergent Synthesis of α-Chiral Tertiary Azides through Catalytic Asymmetric Michael Addition
- 20 October 2020
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 22 (21) , 8578-8583
Abstract
A diastereodivergent synthesis of α-chiral tertiary azides through catalytic enantioselective Michael addition of α-azido indanones to β,γ-unsaturated α-ketoesters is described. The merger of a newly designed bifunctional phosphoramide C4b and hexafluoroisopropanol (HFIP) affords syn-adducts, whereas the use of thiourea C6a provides anti-adducts without the aid of HFIP. Notably, additive HFIP proves to be the key control element to achieve diastereoselectivity reversal in the former case. The products are readily converted to enantioenriched spiro N-heterocycles.Keywords
Funding Information
- Ministry of Education of the People's Republic of China
- Science and Technology Commission of Shanghai Municipality (20JC1416900)
- National Natural Science Foundation of China (21725203, 21901074, 21971067)
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