Synthetic Approach Towards Enantiopure Cyclic Sulfinamides
CONTENTS General Information ........................................................................................................................................... S2 Stereochemical model for epimeric substrates........................................................................................ S2 General scheme for synthesis of the starting allyl halides 1a–m-Br............................................... S3 General procedure A for propargylation of N-sulfinyl imines S1a-c,e-g,j,k ..........................S4 General procedure B for hydroxymethylation of alkynes S2a-c,e-g,j,k ..................................S9 General procedure C for reduction of propargylic alcohols S3a-c,e-g,j,k. .......................... S13 General procedure D for allylation of N-sulfinylimines S1d,h,i. ............................................. S18 General procedure E for cross metathesis with methyl acrylate. ........................................... S21 Synthesis of ester S6l. ....................................................................................................................... S23 General procedure F for reduction of unsaturated esters S6d,h,i,l,m with DIBAL-H..... S25 General procedure G for Appel reaction ........................................................................................... S28 Synthesis of epi-1a-Br .................................................................................................................................... S35 Synthesis of epi-1d-Br.................................................................................................................................... S37 Synthesis of allylic bromide 6. ..................................................................................................................... S41 General procedure H for SN2’-type cyclization of allylic bromides 1a–m, epi–1a,d and 6 . S43 Gram-scale synthesis of cyclic sulfinamide 3g from allylic iodide 1g-I....................................... S53 Compounds from the optimization Table 1 ............................................................................................ S54 Synthetic modifications of the cyclic sulfinamide scaffold ............................................................... S57 Crystal data and structure refinement for sulfoximine 2a ............................................................... S63 Crystal data and structure refinement for sulfoximine 2g ............................................................... S64 Crystal data and structure refinement for sulfinamide 3e ............................................................... S65 Crystal data and structure refinement for sulfinamide 3k............................................................... S66 Crystal data and structure refinement for sulfonimidamide 15 .................................................... S67 References ........................................................................................................................................................... S68 1H, 13C, selected NOESY NMR spectra and HPLC chromatograms for 3k ................................... S69
Pieteikuma datums
16.06.2022.
Atslēgas vārdi
Synthetic Approach Towards Enantiopure Cyclic Sulfinamides
Hipersaite
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.2c01738/suppl_file/ol2c01738_si_001.pdf
