A high-yield regiospecific synthesis of keto oximes from aryl-conjugated ethylenes and ethyl nitrite in the presence of cobalt complex and BH4- ion

Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins

“…235 Their substrate scope was slightly expanded, and included substituted styrenes, 1-phenyl-1,3-butadiene, and some cyclic aryl-conjugated ethylenes. Use of EtONO improved the yield of this reaction considerably (> 90% for styrenes) while halving the catalyst loading and permitting use of NaBH 4 in a few cases.…”

Synthesis of α-Nitro Ketoximes from Styrenes and tert-Butyl Nitrite

“…[15] Okamoto and Tanimoto have shown that using a Co complex as the catalyst, and BH 4 -as the hydrogen donor, the reaction of ethyl nitrite with styrenes can produce oximes as the exclusive product. [16] In 1998, Sugamoto was able to effect the same transformation using Et 3 SiH as the hydride donor employing Co Ⅱ (tpp) as the catalyst. [17] This was later extended by Beller to use Fe(pc) as the catalyst.…”

Catalytic Asymmetric Hetero Diels–Alder Reactions of N‐Sulfinyl Dienophiles with Chiral Bis(oxazoline)copper(II) and ‐zinc(II) Triflates

“…Under the influence of the Lewis acids, reactions with the dienes 7 – 10 provided the cis isomers as the major products. For the unsymmetrical dienes 8 and 9 ,17 only the 3‐substituted regioisomers 12 and 13 , respectively, were formed. Similar results have been published for the uncatalyzed HDA reactions of N ‐sulfines 1 (X = Ts, COTol) with 1‐substituted dienes (R′ = Me, Ph, p ‐NO 2 Ph, p ‐MeOPh), which usually provided the kinetically favored 3‐substituted 1,2‐thiazine 1‐oxides at low temperature (5 °C) and the less crowded, thermodynamicallyfavored, 6‐substituted products at higher temperature (80 °C) 2e,18…”

“…The uncatalyzed HDA reaction of 10 17,19 with N ‐sulfine 1a or 1b at room temperature for 22 h afforded mixtures of stereoisomers and regioisomers. For 1a , a mixture of cis ‐ 14a , trans ‐ 14a , cis ‐ 15a , and trans ‐ 15a was formed in a ratio of 1:3.1:1:7.1 and in 86 % total yield.…”