Enantioselective Catalysis CXXI [1]: Chiral Phosphane Ligands with Additional Oxygen Functionalities

Chirally N-Substituted Indole-2-carbaldehydes. Preparation and Use in Asymmetric Synthesis

“…In both molecules of 6a they are symmetrical with an average of 0.32 Å whereas in 5b they are 0.18 and 0.43 Å. The phenyl ring C(14)-C (19) is twisted relative to plane 2 by about the same in all of the molecules (the corresponding dihedral angle being 31.5° (5b) (2) 1.393 (5) 1.380(5) C(8)−C (9) 1.511 (2) 1.500 (6) 1.507(5) C(9)−C (10) 1.535 (2) 1.533 (6) 1.523(6) C(10)−C (11) 1.519 (2) 1.513 (7) 1.517(7) C(11)−O(1) 1.223 (2) 1.232 (6) 1.222(5) C(11)−C (12) 1.435 (2) 1.417 (8) 1.417(7) C(12)−C (13) 1.356 (2) 1.347 (7) 1.338(7) C(13)−N (2) 1.361 (2) 1.348 (6) 1.359(6) N(2)−C (9) 1.473 (2) 1.477 (6) 1.477(6) N(2)−C (14) 1.423 (2) 1.417 (6) 1.411 (6) The geometric parameters for the molecules are identical. Several bond lengths are given in Table 2.…”

“…The Mitsunobu conditions with complete inversion of configuration [7]. For this work racemic 1-phenylethanol and optically active (R)-2-methoxy-1-phenylethanol ([α] D 25 -32.1° (c 1.4, CH 2 Cl 2 ), enantiomeric excess 63%) [8,9]) were used for alkylating 2-cyanoindole in the presence of PPh 3 and diisopropyl azodicarboxylate (DIAD). The alkylation products 3a,b were obtained in high yields.…”