Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 17, Pages 9795-9817Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01315
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Funding
- Department of Science and Technology (DST), SERB, New Delhi [EMR/2015/000860]
- SERB, DST (New Delhi) [PDF/2015/000454]
- University Grants Commission (UGC) (New Delhi)
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An organocatalytic reductive coupling and Lewis-acid-catalyzed annulative ring-opening strategy is developed as a two-step protocol for the stereoselective synthesis of dihydropyrans as the major products from the chiral formylcyclopropanes, CH acids, and Hantzsch ester. It is an efficient, catalytic, two-step protocol for the chiral synthesis of dihydropyrans and dihydrofurans. Structurally important and challenging functionally rich cyclopropanes containing cyclic-1,3-diones were synthesized in very good yields with excellent chemo-, enantio-, and diastereoselectivities from the readily available starting materials, chiral formylcyclopropanes, cyclic-1,3-diones, or CH acids and Hantzsch ester through an organocatalytic reductive coupling reaction at ambient conditions, especially without harming the cyclopropane ring. Chiral cyclopropanes containing cyclic-1,3-diones were stereospecifically transformed into dihydropyrans and dihydrofurans found in many bioactive natural products and drugs through an annulative ring-opening reaction by using Lewis-acid (BF3 center dot OEt2) or cesium carbonate (Cs2CO3) catalysis. Highly diastereo- and regioselective ring opening of cyclopropanes was explained through a stereospecific intimate ion pair pathway.
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