Science of Synthesis

Bräse, S.; Lesch, B.; Zimmermann, V., Science of Synthesis, (2010) 41, 554.

Optically active β-azidocarboxylic acids ‌45‌ have been prepared by nucleophilic azide-mediated ring opening of the corresponding optically active β-lactones ‌44‌ with retention of enantiopurity (‌Scheme 15‌; see also ‌Scheme 12‌, Section ‌41.8.1.5.1‌).[‌52‌]

‌Meeeee 88‌ Meeee-Meeeeeee Meee Meeeeee ee β-Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e e.e. = eee eeeeeeee.

Meeeeeeee ee 8-eeeeeeeeeeeeeeeeee eeeeeeeeee eeee ee ‌88‌ ee eee eeeeeeee ee e eeeeeeeee(8) eeeeeeee eeeee 8-eeeeeeeeeeeeeeeeee eeeeee ee eeee ‌88‌, eeeeee eeee eeeeeeeee ee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Me eee eeeeeeeeeee eeeee, eee eeeee eeeee eeeeeeeeee eee eeeeeeeeeeee eeeeeee ‌88‌ eeee eee eeeeeeeeee eeee eeeeeeee eeee (eeeeeeee ee eee eeeee eeeeeeeee–eeeeee eeeeeee). Meeeee eeeeeeeeeee eeeeeeeeee eeee eee eee eeee ee eeee eeeeeeeeeeeee ee eeee ‌88‌ eeeeee eeeeeeeeeee eeeeee eeee eeeeeeeee ee eee eeeeeeeeeeeee (MM8) ee eeeee eeeeee eee eeee eeeeeee (MM8).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee e Meeeeeeeeee Meeee eeee e 8-Meeeeeeeeeeeeeeeee 8-Meeeeeeeeeeeeeee Meeee Meeeeeeee(8) Meeeeeeee[‌88‌]

Meeeeeeee, eeeeeeeeeeeeeeee eeeeeeeee(8)-eeeeeeeee eeeeeeeee ee eeeeeeeeee eee-eeeeeeeeeee eee eeee eeeeeee ee eeeeeee eeeeeeeeeee eeeee eeeeee ee eeee eeeeee.[‌88‌]

Meeeeee (M)-eeeeeeeeeee eeeeeeeeee eee eeeeeee (M)-α-eeeeeee eeeee eeeeeeeeee eeee ee ‌88‌ eee eeee eeeeeeee eeeeeeeeee eee eeeeeeeee(8)-eeeeeeeee eeeeeee eeeeeeeee eeeeeeeee.[‌88‌] Meeeeee (M)-eeeeeeeeeee eeeeeeeeee eeeeeee eeeeee eeeeeeeee eeeeeeee ee M- eee M-eeeeeee ee γ-eeeee α,β-eeeeeeeeeee eeeeeeee eeee eeeeeeeeeeee eeeeeeee eeeeeee eeee 88 ee 88%, (M)-α-eeeeeee eeeee eeeeeeeeee ‌88‌ eeeee eeeeeeeeeee M-eeeeeee ee γ-eeeee α,β-eeeeeeeeeee eeeeee ‌88‌ eeee 88% ee (‌Meeeee 88‌). Mee eeeeeeee eeeeeeeeee eee eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ‌88‌ ee eeeeeeee eeee eeeee eeeeeeeeeeeee eee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeeeeeeeee Meeeeeeeeee ee (M,M)-γ-Meeee α,β-Meeeeeeeeee Meeeee ee Meeeeeeee(8) Meeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeee Meeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeee eee eeeeeee ee eeeeeee eee ee eeeeee eeeee. Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

Me e eeee ee MeM8 (88 ee, 8.8 eeee) ee eee MMMM (8.8 eM) ee 88°M eee eeeee β-eeeeeee ‌88‌ (8.8 eeee) eee eeeeeee. Mee eeeeeeeeeee ee eee eeeeeeee eeeeeeee eee eeeeeeeee ee MMM (∼8 e). Mee. ee MeMMM8 (8 eM) eee eeeee ee ee. Mee eeeeeee eee eeeeeeeeee eeee M8M eeeee eee eee eeeeeeeeeeee eeeee eeeeeeeee. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8×8 eM), eee eee eeeeeee eeeee eee eeeeeeeee eeee 8 M MMe eee eeeeeeeee eeee eeeeeeeeee MeMMe (8×8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee M8M (8×8 eM) eee eeeee (8×8 eM), eee eeee eeeee (Me8MM8). Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee eee β-eeeee eeee ‌88‌.

Meeee (M,M)-8-Meeeeeeee-8-eeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeee ee eeeee eeeeee eeee eeeee eeeeeeeee eee eeeeee eeeee eee eeeeeeeee eeeeeeeee eeee.

Me e eeee ee eeeee (M,M)-8-(eeeeeeeeeeeeeeeee)eeee-8-eeeeee (‌88‌, M8 = Me; 888 ee, 8.888 eeee), MMMM8 (88.8 ee, 8.88 eeee), eee Me8M (8.8 ee, 8.888 eeee) ee eeeeeee eeeeeeeee MM8Me8 (8.88 eM) ee 8°M eee eeeee Me8(eee)8 (8.8 ee, 8 μeee). Mee eeeeeee eee eeeeeee ee 8°M eee eee eeeeeeee eee eeeeeeeee ee MMM (eeeeee eee, MM8Me8/eeeeeee 8:8). Meeee 8.8 e, eee eeeeeee eee eeeeeee eeee Me8M eee eee eeeeeeee eeeeee eee eeeeeeee eeeeeee e eeeee eeeeee eee eeee eeeeeee eeee MeMM8 (MeMM8/eeeeee eee 8:8) eee eeeeee eeee Me8M. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (8-ee eeeeee eee eeeee, MM8Me8/eeeeeee 8:8) ee eeee e eeeeeeeee eee; eeeee: 88 ee (88%); 88% ee.

References