0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via Reactions with Chiral Silyl Enol Ethers

DOI: 10.1055/sos-SD-202-00309

Liu, L.; Wang, D.; Li, C. -J.Science of Synthesis: Stereoselective Synthesis, (20112601.

An efficient synthetic route has been developed for the synthesis of enantioenriched 3-hydroxy-2-methylpropanoates (e.g., 63) using N-methylephedrine ester as a chiral auxiliary group to form chiral silyl ketene acetals (e.g., 19) via the condensation product 62 (Scheme 27).[‌13‌] By this route α-amino and α-hydrazino acids,[‌56‌] as well as trans-β-lactams[‌57‌] have been synthesized in high enantiomeric excess and good chemical yields.

Meeeee 88 Meeeeeeeeeeeeeeeee Meeeeeeee Meeee Meeeeeee Meeee e Meeeee Meeee Meeeee Meeeee Meeeeee eeee M-Meeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeee (8M,8M)-8-Meeeee-8-eeeeeee-8-eeeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeee ee eeeeeeeee ee eeeee, eeeeeeee, ee eeee, eee ee eeeeee eeeee ee eeeeeeeeee.

M eeee ee MeMMM (8eeee) ee MM8Me8 (8eM) eee eeeeeee eeee 8.8M MeMe8 ee MM8Me8 ee 88°M, eeeee M8, eeee eeeeeeee. Meeeeeeeeee eeeee eeee, e 8.8M eeee ee eee eeeee eeeeee eeeeee 88 ee MM8Me8 (8.88eM) eee eeeeee eeeee ee 88°M. Meeee 8e ee 88°M, eee eeeeeee eee eeeeeeee eeee 8% MeMMM8 eee 8.8M ee MeMM eee eeeeeeee eeeeeee Meeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee MM8Me8, eee eee eeeeeeee eeeeeee eeeeeeee eeee eeeee eee eeeeeeeeeeee ee eeee eee eeeee eeeeeeeeeeee eeeeeee 88; eeeee: 88%; eeeee (eeee/eee) >88:8; ee (eeee-eeeeee) >88:8.

M eeee ee eee eeeee eeeeeeeeeeee eeeeeee 88 (8.8eeee) ee MeMM/M8M (8:8; 88eM) eee eeeeeee eeee MeMM (888ee, 88.8eeee) ee ee, eeee eeeeeeee. Meeee 88e ee ee, eee eeeeeee eee eeeeeee eeee M8M (8eM), eee MeMM eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eeeeeee eeeeeee eee eeeeeee eeee 8M MMe (88eM) eee eeeeeeeee eeee MM8Me8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeee eee eeeeeeeeeeee ee eeee eee eeeee eeee. M eeee ee eee eeeee eeee ee Me8M/MeMM (8:8) eee eeeeeee eeee MM8M8 ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8); eeeee: 88%; 88% ee. [α]M88 +88.8 (e 8.88, MMMe8). Meeeeeeeeee M-eeeeeeeeeeeeeee eee eeeeeeeee.