Periodic Reporting for period 4 - CatHet (New Catalytic Asymmetric Strategies for N-Heterocycle Synthesis)
Reporting period: 2019-10-01 to 2020-03-31
Based upon the catalytic generation and trapping of unique or unusual classes of organometallic intermediate, we have developed several new synthetic methodologies. Key highlights are:
(1) A new route to 7-membered heterocyclic ring systems has been defined (J. Am. Chem. Soc. 2015, 137, 8054-8057).
(2) A versatile entry to substituted diazepanes has been developed (J. Am. Chem. Soc. 2016, 138, 11465-11468).
(3) Bifunctional amine reagents have been developed in the context of new aza-Heck reactions (Angew. Chem. Int. Ed. 2016, 55, 11198-11202).
(4) New classes of cyclopropane have been identified for C-C activation based cycloaddition (J. Am. Chem. Soc. 2016, 138, 13501-13504).
(5) The first examples of highly enantioselective aza-Heck cyclizations have been developed (Chem. Sci. 2017, 8, 1981-1985).
(6) We have developed TFA promoted C-N bond forming dearomatization reactions (J. Am. Chem. Soc. 2017, 139, 14005-14008).
(7) We have developed base promoted C-N bond forming dearomatization reactions (Angew. Chem. Int. Ed. 2017, 56, 14531-14535).
(8) We have developed a direct synthesis of lactones and lactams (Angew. Chem. Int. Ed. 2017, 56, 13824-13828).
(9) We have reported the first aza-variant of the Prilezhaev epoxidation (J. Am. Chem. Soc. 2018, 140, 17846-17850).
(10) We have reported aza-Heck reactions of carbamate protected systems (Angew. Chem. Int. Ed. 2018, 57, 5124-5128).
(11) We have developed a modular route to azepines (J. Am. Chem. Soc. 2018, 140, 2743).
(12) A method for the ortho- and enantioselective alkylation of anilides with styrenes or α-olefins has been developed (J. Am. Chem. Soc. 2018, 140, 9351-9356).
(13) An broad scope enantioselective aza-Heck reaction has been developed (J. Am. Chem. Soc. 2019, 141, 3356-3360).
(14) Multicomponent cycloaddations of electron poor cyclopropanes have been developed (Angew. Chem. Int. Ed. 2019, 58, 221-225).
(15) A method for the preparation of 8-membered heterocycles has been reported (Angew. Chem. Int. Ed. 2019, 58, 18844-18848).
(16) A strategy for the preparation of complex polyheterocycles has been developed (J. Am. Chem. Soc. 2020, 142, 1740-1745).
The work has been disseminated in top journals (as outlined above) and via >40 seminars to academia, international conferences and industry (throughout Europe, North America and Asia).