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27.15.2.4.2 Neber Reaction

DOI: 10.1055/sos-SD-127-00117

Chiba, S.; Narasaka, K.Science of Synthesis Knowledge Updates, (20114478.

Since its discovery in 1926,[‌489‌] the Neber reaction of O-sulfonyloximes with base has been recognized as one of the promising methods for the preparation of α-amino ketones (Scheme 48).[‌490‌] Combination of O-tosyloximes with sodium ethoxide or pyridine is the most common example of this reaction. The intermediate of the Neber reaction, a 2H-azirine 57, can be isolated and used for further transformations.[‌491‌]

Meeeee 88 Meeeeeeeee ee M-Meeeeeeeeeeeee eeee α-Meeee Meeeeee[‌888‌]

Meeee eee eee eeeeeeeeeee eeeeeeeeee eee eeeeeee eeeeeeeee: (e) eeeeeee eeeeeee ee ee α-eeeeee ee eee eeeee, eeeeeeee ee eeee ee eee eeeeeeeee eeeeee ee eeee e eeeeeee eeeeeeeeeeee eeeee eeeeeee eeee eee ee8 MM, ee (ee) eeeeeeeee eeeeeeeeeeee eeeeeeeeeeee eeee eee α-eeeeee ee eee eeeeeeee eeee.[‌888‌] Mee eeeeeee eeeeeeeeeeee ee eeeeeeee ee eee eeeeeeee eeeeeee eee ee α-eeeeeee, eeeeeeeeeeee ee eee eeeeeee eeeeeeeeeeeeeee ee eee M-eeeee­eeeeeeee. Meeeeeee eeeeeeeeeeeee eee eeeeeeeeeeeee ee eeee eeeeeeee eee eeeee ee eeee eeeeeeeee. Meeeeeeee eeeeeeee (eeeeeeeeeee eeeeeeeeeeeeeeee/eeeeeeeeeeeeeeeeee) eee ee eeeeeee eee eee 8M-eeeeeee eeeeeeeee eeee α-eeee eeeeeeeee.[‌888‌] Meeeeeeeee Meeee-eeee eeeeeeeee eeee eeee eeeeeeee, eeeee eeeeeeeeeeeeeeee eeeeeeee 8M-eeeeeeee (e.e., 88) (Meeeee 88)[‌888‌] eee α-eeeee eeeeeee eeee eeee eeeeeeee eeeee eeeeee eeeeeeee eeeee,[‌888‌,‌888‌] eeeeeee-eeeeeeeee eeeeee eeeeee,[‌888‌] ee eeeeee eeeee-eeeeeeee eeeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeeee Meee Meeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

()-Meeeee 8-Meeeee-8M-eeeeeee-8-eeeeeeeeeee (88, M8=M8=Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee eeeeeeeee (888ee, 8.888eeee) ee eeeee eeeeeee (88eM), e eeee ee eeeeee 8-[(eeeeeeee)eeeee]eeeeeeeee [eeeeeee ee eee eeeeeeeeeeeee (88:88); 888ee, 8.888eeee] ee eeeee eeeeeee (88eM) eee eeeee eeeeeeee ee 8°M. Meeee 88e, 8.88Mee MMe (88eM) eee eeeee. Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee ee eeee eee eeeee eeeeeee (888ee). Mee eeeee eeeeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee (88°M/8Meee) ee eeee eee eeeeeee ee e eeeeeeeee eeeeee (88% eeee eeeeeeeee ee MMM); eeeee: 88.8ee (88%); 88% ee; [α]M88 -88.8 (e 8.8, MMMe8).

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