A concise enantioselective synthesis of pyrrolidine sedum alkaloids (R)-(R)-(+), (S)-(S)-(−)-pyrrolsedamine and (S)-(R)-(+)-pyrrolallosedamine by using proline catalysed α-amination reaction

Diastereo‐ and Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols in Two Steps from Terminal Alkynes

“…[26] TBS protection of the hydroxy group of 5aa [27] followed by oxidation of the B À Cbond with NaBO 3 afforded g-siloxy aldehyde 12,which is acommon intermediate for the synthesis of pyrrolidine sedum alkaloids (À)pyrrolsedamine and (+ +)-pyrrolallosedamine. [28] (À)-g-Dodec-alactone (13), which was originally isolated from rove beetles as ad efensive secretion, was stereoselectively synthesized from 5ia through sequential double oxidation with NaBO 3 and PCC. [29] In summary,w eh ave developed an efficient method for the diastereo-and enantioselective synthesis of (E)-d-borylsubstituted anti-homoallylic alcohols via 1,1-di(boryl)alk-1enes from terminal alkynes.The use of terminal alkynes as the starting materials is akey advantage to our method, presenting better chances of application to synthetic enterprises.…”

Diastereo‐ and Enantioselective Synthesis of (E)‐δ‐Boryl‐Substituted anti‐Homoallylic Alcohols in Two Steps from Terminal Alkynes

“…Treatment of 5 aa with an excess (4.0 equiv) of CuCl 2 resulted in the formation of alkenyl chloride 11 with its geometrical integrity maintained ( E / Z >95:5) . TBS protection of the hydroxy group of 5 aa followed by oxidation of the B−C bond with NaBO 3 afforded γ‐siloxy aldehyde 12 , which is a common intermediate for the synthesis of pyrrolidine sedum alkaloids (−)‐pyrrolsedamine and (+)‐pyrrolallosedamine . (−)‐γ‐Dodecalactone ( 13 ), which was originally isolated from rove beetles as a defensive secretion, was stereoselectively synthesized from 5 ia through sequential double oxidation with NaBO 3 and PCC …”

Solvent‐Induced Self‐Assembly of Naphthalenediimide Conjugated to Tetraphenylethene through D‐ and L‐Alanine

“…These properties render NDI as one of the favourite building blocks to fabricate supramolecular nanostructures via selfassembly. The diverse supramolecular architectures such as nanotubes, [10] nanospheres, [11] nanofibers, [12] nanobelts, [13] vesicles, [14] golf-balls, [15] nanocups, [16] catenanes, [17] rotaxanes, [18] flowers, [19] and helical assemblies [20][21][22] under various conditions have been reported in literature. These supramolecular structures have potential of applications in organic photovoltaics (OPV), [23] organic field effect transistors (OFETs), [24] dye sensitised solar cells (DSSCs), [25] and light harvesting.…”