Regio- and stereoselective 6- exo - trig radical cyclisations onto chiral perhydro-1,3-benzoxazines: synthesis of enantiopure 3-alkylpiperidines

Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpen Aminodiols

“…Monoterpene-based aminodiols have been demonstrated to be excellent chiral auxiliaries in a wide range of stereoselective transformations, including Grignard addition [18,19], intramolecular [2 + 2] photocycloaddition [20], and intramolecular radical cyclization [21]. Although monoterpene-based 3-amino-1,2-diols are well-known compounds, their sesquiterpene or diterpene analogues are still not known in the literature.…”

“…To develop new, efficient, and commercially available chiral catalysts, chiral natural products, including (+)-and (−)-α-pinene [10,11], (−)-nopinone [12], (+)-carene [13,14], (+)-sabinol [15], (−)-pulegone [16], or menthone [17], can serve as important starting materials for the synthesis of aminodiols. Monoterpene-based aminodiols have been demonstrated to be excellent chiral auxiliaries in a wide range of stereoselective transformations, including Grignard addition [18,19], intramolecular [2 + 2] photocycloaddition [20], and intramolecular radical cyclization [21].…”

Regio‐ and Stereoselective Synthesis of Bicyclic Limonene‐Based Chiral Aminodiols and Spirooxazolidines

“…A large number of natural products such as α‐ and β‐pinene, 2‐ and 3‐carene, and (+)‐pulegole serve as important starting materials for the synthesis of bi‐ and trifunctional chiral compounds and heterocycles. Monoterpene‐based 1,2‐ and 1,3‐amino alcohols have been demonstrated to be excellent chiral auxiliaries in a wide range of stereoselective transformations, including intramolecular radical cyclizations, intramolecular [2+2] photocycloaddition, and Grignard addition …”

“…[1][2][3] Al arge number of natural products such as a-a nd b-pinene, [4][5][6] 2-and 3-carene, [7,8] and (+ +)-pulegole [9,10] serve as important startingm aterials fort he synthesis of bi-and trifunctional chiral compounds and heterocycles. Monoterpene-based 1,2-and 1,3-amino alcohols have been demonstrated to be excellent chiral auxiliaries in aw ide range of stereoselective transformations, including intramolecular radical cyclizations, [11] intramolecular [2+ +2] photocycloaddition, [12] and Grignard addition. [13,14] Furthermore,a minodiols, combining the chemical properties of 1,2-and 1,3-amino alcohols derived fromn aturally occurring terpenes, are excellent startingm aterials and catalysts of stereoselectives ynthesis.…”

Stereoselective syntheses and application of limonene- and isopulegol-based bi- and trifunctional chiral ligands

“…19 Furthermore, alanine transporters were found to be highly upregulated in antibody-producing cell lines indicating the cell's requirement for this amino acid. 18 Monoterpene-based 1,2-and 1,3-amino alcohols have been demonstrated to be excellent chiral auxiliaries in a wide range of stereoselective transformations including intramolecular radical cyclizations, 20 intramolecular [2+2] photocycloaddition, 21 and Grignard addition. 22,23 Besides their value in enantioselective catalysis, 1,2-and 1,3-amino alcohols are also excellent building blocks for the synthesis of various heterocyclic ring systems, such as 1,3-oxazines, 1,3-thiazines or 1,4-oxazepams.…”