Catalytic Asymmetric Acyl Halide‐Aldehyde Cyclocondensation Reaction

Abstract

( S )‐Valinol Triethylamine Trifluoromethanesulfonic anhydride ( S )‐ N ‐Trifluoromethylsulfonyl‐2‐isopropylaziridine Benzylamine (2 S ,6 S )‐4‐Benzyl‐1,7‐bis(trifluoromethylsulfonyl)‐2,6‐disopropyll‐1,4,7‐triazaheptane Disiopropylethylamine Trimethylaluminum Acetyl bromide Hydrocinnamaldehyde (4 S )‐4‐(2‐Phenethyl)oxetane‐2‐one

Development of a Practical Synthesis of a Farnesyltransferase Inhibitor

“…Instead, aziridine 20 was obtained as the major product (90%), which presumably resulted from formation of sulfonate 19 followed by intramolecular S N 2 reaction (Scheme ). Formation of 19 was kinetically favored over formation of sulfonamide 13 due to the higher reactivity of the primary hydroxyl group versus the hindered secondary amine. Using pyridine as solvent at room temperature with excess 2-thienylsulfonyl chloride (3 equiv) generated a complex mixture (3:5:8:2:2) of 13 , 20 , 23 , 24 , and 21 via the reaction sequences shown in Scheme .…”

The Reactions of Alkenes with Phenyl-N-triflylimino-λ3-iodane: Solvent and Oxidant Impact

“…1 H and 13 C chemical shifts (δ) are reported in parts per million (ppm) relative to the residual solvent peak of CDCl 3 (δ = 7.27 ( 1 H) and 77.10 ( 13 C) ppm, respectively). 19 F NMR chemical shifts (δ) are given relative to CCl 3 F. All coupling constants (J) are reported in hertz (Hz). Abbreviations are s, singlet; d, doublet; t, triplet; q, quartet; and brs, broad singlet.…”

“…13 C NMR (CDCl 3 ): δ 137.04 (C u ), 129.22 (C m ), 129.13 (C p ), 126.26 (C o ), 121.25 (q, J = 321.2 Hz, CF 3 ), 58.99 (CHN), 36.49 (CH 2 Br). 19 2-Iodo-1-phenylethan-1-ol (5) Violet liquid, 0.06 g (12%). Identical to that in [30].…”

“…13 C NMR (CDCl 3 ): δ 168.59 (C=N), 119.88 (q, CF 3 , J = 320.6 Hz), 48.65 (CH 2 N), 43.82 (CH), 43.17 (CHI), 32.05, 32.03, 26.09, 25.91 (CH 2 ), 22.47 (CH 3 ). 19 The reaction was performed and treated as above. The residue after solvent removal was poured with ether, kept for 1 h in a fridge, and the precipitated succinimide was filtered off.…”

“…N-Triflylaziridine was also obtained by treating (2S)-2-amino-3-methylbutan-1-ol with triflic anhydride on strong cooling (Scheme 1, route 2) [19].…”