New Reactions Methods
37. Formal inversion of a steroidal C13 quaternary center in the context of completing the total synthesis of a rare marine-derived pregnene (Org. Lett. 2021, 23, 2248-2252).
36. Intramolecular coupling between alkynes and diketones for the stereoselective assembly of a variety of polyclic carbocycles (Org. Lett. 2019, 21, 6126-6129).
35. Double asymmetric Friedel–Crafts cyclization and oxidative rearrangement as an entry to tetracyclic terpenoid motifs (Nature Communications, 2019, 10, article #2448 (DOI: 10.1038/s41467-019-10415-6)). For press release links, see: Dartmouth and AAAS EurekAlert.
34. An intramolecular annulation reaction between alkynes and b-keto esters for the synthesis of fully-substituted cyclopentenones (Org. Lett. 2019, 21, 567-570).
33. Chemoselective [2+2+2] annulation for the synthesis of functionalized hydrindanes – it is demonstrated that an alkoxide present on a diyne-containing coupling partner controls the course of the coupling reaction (Arkivoc 2018, 132-138).
32. A new approach to the de novo synthesis of partially aromatic steroids is described that features a combination of one of our metallacycle-mediated annulation reactions and a new acid-mediated rearrangement/cyclization reaction that establishes the steroidal B-ring (Nature Chem. 2018, 10, 70-77).
31. Synthesis of highly oxygenated carbocycles by stereoselective coupling of alkynes to 1,3- and 1,4-dicarbonyl systems (J. Am. Chem. Soc. 2017, 139, 12374-12377).
30. Synthesis of angularly substituted trans-fused decalins by a metallacycle-mediated annulative cross-coupling cascade (Angew. Chem. Int. Ed. 2016, 55, 13099-13103).
29. Convergent synthesis of angularly substituted decalins by metallacycle-mediated annulative cross-coupling.
28. Vinylcyclopropanes by metallacycle-mediated cross-coupling between cyclopropenes and alkynes.
27. Angularly substituted cis-fused hydrindanes by metallacycle-mediated annulative cross-coupling/oxidation between alkynes and 1,6-enynes and IPNBSH mediated reduction.
26. Angularly substituted trans-fused hydrindanes by metallacycle-mediated annulative cross-coupling between alkynes and 1,6-enynes.
25. Cross-conjugated triene-contatining hydrindanes by metallacycle-mediated annulative cross-coupling and use of products in intermolecular [4+2].
24. Angularly substituted hydrindanes by metallacycle-mediated annulative cross-coupling between alkynes and 1,6-enynes.
23. Deoxypropionates by metallacycle-mediated alkyne–allylic alcohol coupling and stereoselective hydrogenation.
22. Regiospecific synthesis of substituted pyridines by metallacycle-mediated imine–allylic alcohol coupling, intramolecular cyclization and oxidation.
21. Stereoselectivity in intramolecular [3+2] cycloaddition of homoallylic nitrones.
20. Synthesis of primary homoallylic amines by metallacycle-mediated coupling of TMS-imines (generated in situ) with allylic alcohols.
19. Skipped polyenes by chemo-, regio- and stereoselective coupling between alkynes and 1,5-dienes.
18. Skipped trienes via metallacycle-mediated vinylcyclopropane–alkyne cross-coupling.
17. Quinolizidines and indolizidines by metallacycle-mediated allylic alcohol–imine coupling and aza-Sakurai.
16. Exo-alkylidene γ-lactams by imine–allylic alcohol coupling and Pd-catalyzed carbonylation.
15. Piperidines by metallacycle-mediated alkyne–imine cross-coupling and iminium ion-based cyclization.
14. (Z)-homoallylic amines through metallacycle-mediated allylic alcohol–imine coupling.
13. (E)-anti-homoallylic amines through metallacycle-mediated allylic alcohol–imine coupling.
12. A stereochemically complementary process to the Claisen rearrangement: Stereoselective coupling/oxidation between allylic alcohols and vinylsilanes.
11. Metallacycle-mediated coupling between allenes and imines: Stereoselective synthesis of dienylic amines
10. (Z)-selective synthesis of 1,4-dienes by metallacycle-mediated allylic alcohol–alkyne cross-coupling.
9. (E)-selective synthesis of 1,4-dienes by metallacycle-mediated allylic alcohol–alkyne cross-coupling.
8. 1,5-amino alcohols and piperidines by metallacycle-mediated alkene–imine cross-coupling.
7. Metallacycle-mediated coupling between alkynes and allenes: Stereoselective synthesis of cross-conjugated trienes.
6. Metallacycle-mediated coupling between alkynes and allenes: Stereoselective synthesis of 1,4-dienes.
5. Tetrasubstituted α,β-unsaturated γ-lactams from alkyne–imine coupling.
4. First regio- and stereoselective metallacycle-mediated alkene–alkyne cross-coupling.
3. First regioselective cross-coupling between internal alkynes.
2. Regioselective alkyne–alkyne cross-coupling for polypropionate assembly.
1. Regioselective alkyne–aldehyde coupling for polypropionate assembly.
