Navigation

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
2.6.1.1 Addition of Sulfur Ylides

DOI: 10.1055/sos-SD-202-00130

Aggarwal, V. K.; McGarrigle, E. M.; Shaw, M. A.Science of Synthesis: Stereoselective Synthesis, (20112311.

Sulfur ylides can react with aldehydes and ketones to form epoxides {see Science of Synthesis, Vol.37 [Ethers (Section 37.2.3.3)]} and the ylides can be subdivided on the basis of stability {Science of Synthesis, Vol.27 [Heteroatom Analogues of Aldehydes and Ketones (Section 27.1)]}. Stabilized sulfur ylides only react with carbonyl compounds to form epoxides under certain conditions. Ester-stabilized ylides require specialized conditions to react with aldehydes[‌1‌] but will react with 1,2-dicarbonyl compounds.[‌2‌] Carboxylate-stabilized ylides form epoxides with high trans selectivity, but only modest enantioselectivity.[‌3‌] Amide-stabilized sulfur ylides react with aldehydes with high trans selectivity[‌4‌] and enantioselectivity;[‌5‌] substrate control can also give rise to good control of stereogenic centers.[‌6‌]

Mee eeeeeeee ee eeeeeeeeeeeeee eeeeeeeee eeeeee ee e eeee eeeeee eeeeee eee eee eeeeeeeeeeeeeee eeeeeeeee ee eeeee-eeeeeeee. Me ee eeeeeeeeeee ee eeeeeee eee eeeeeeeeeee eeeee ee eee eeeeeeeeeeeeeeeee eeee eee ee eeeeeeee ee eeeee eeeeeeeeeeee (Meeeee 8). Mee eeeeeeee ee ee eeeee eeee e eeeeeeee eeeeeeee eeeee e eeeeeee. Me eee eeee ee eeeeeeeeeeeeee eeeeee eeeeee eee eeeeeeeee eeeeee eeeeeee 8M/8M eeeee ee eeee eee eeeeeeeeee eeeeeee eeeeeeeee eeeee eee eeeeeeeeee eeeeeee eeeeeeee eeeee eee eeeeee ee eeee eeeee.[‌8‌] Meeeeeee eeeeee eee MM eeee eeee eeee eeee eeeee ee eeee 8M/8M, eeeee eeeeeee eeee eeeeeee ee eeee eeeeeeee 8/8. Mee eee ee eeeeeeeee eeee eeeee eeeeeeeeeee ee eeeee eeeeeeee eeeeeeeeee eeeee eeeee eee eeeeeeeee ee eeee-eeeeeee 8M ee eeeeeeeeeeeee, eee eee eeeeeeeee ee eee-eeeeeee 8M ee eeeeeeeeee.[‌8‌,‌8‌] Mee eeee-eeeeeeee eeee eeee eee eeeeeeeee eeeeee eee-eeeeeee 8M ee 8M eeeee ee ee eee eeee-eeeeeeee eeee eee eeeeeeeee ee eee-eeeeeee 8, eee eeeee eeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeee ee eeeeeeeeeeeee, eee eeee eeeee eeeeeeeeeeeee eee eeeeeeee. Mee eeeee eeeeeeeeee eeee eeeeeeeee ee eee eeeeeeeee ee eee eeeee eee eee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeee eeeeeee eee/ee eee eeeeeeee ee eeeeeee eeeee eee ee eeee ee eeee eee eeeeeeee eeeeeeeeee ee eeee eeeeeeeee eeeee eeeeeeeeeee ee eeee eeeee {eee eee[‌8‌] eee Meeeeee ee Meeeeeeee, Mee.88 [Meeeee (Meeeeee 88.8.8.8)] eee e eeeeeeeeee ee eee eeeeeee eeeeeeeeeee eeeeeeeeeeeee}. Meee, eee eeeee ee eeeee/eee eeeeeeee eee ee eeeeeeeee ee eeeeeeee eee eeeeee ee eeeeee eeeeeee eeee (eeeeeeeeeeee/eeeee/eeeeeee eeeeeeee eee eeeeeeeee eeee eeee eee eeeee ee eeeeee ee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee eeee).

Meeeee 8 Meeeeeeeee Meeee ee Meeeeee Meeeeeeee eeee Meeeeeee Meeeeeeeee eeee MMM Meeeeeeeeeee[‌8‌]

Meee eeeeeeeeeee eeeeeeee eeeeeeeeee eee eeeeeeee ee eee eeeee ee eee eeeeeeee ee eeee eee eeee-eeeeeee ee eeeeeeeeeeeee, eee eee eeeeeeeeeeeeeeeeee ee eeeeeeeeee ee eeee eeee. Meeeeeeeeeeeeeeeee ee eeee eeeeeeee ee eeeee eeee ee eee eeeee ee eeeeeeee. Meee eeeeeeee eeee eeee eeeeeeee ee eeee (e) eeee eee ee eeeee eeee eeeee ee eeeeeeeee; (e) eee eeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeee eee eeeeeeeeee; eee (e) eeee eee eeee ee eee eeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeee ee Meeeee 8.[‌88‌,‌88‌] Meee 8M eee 8M eee eeeeeee eeee 8M eee 8M, eeeeeeeeeeee, eee eeee eee eeee ee eeee eeeee ee eeeeeeeeee, eeeeeee ee eee (M,M)-eeeeeee eeeee eeeeee. Meee eeeee ee eeee eeeeeeeeeeeeeeeeee eeeee eeeeeeeeee eeee eeeee eeeeee. Me eeeeeeeeeee eee ee eeeeeeeee eeee eeeeeeeeeeeeeeeeee ee ee eeeeeee eee eeeeeeeeee ee eee eee eeeee eeeeeeeeee eeeeee eee eeeeeeeee, eee eeee ee eeeeeee ee ee eeeeeeeee eeee eee eeee eeeee eeeeeeee eeeeeeee ee Meeeeee eee Meeeeee.[‌88‌,‌88‌]

Meeeee 8 Meeeeee ee Meeee Meeeeeeeeeee eee Meee Meeeeeeeeee Meeeeee ee Meee Meeeeeeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeeeee Meeeee Meeeee[‌88‌,‌88‌]

Mee eee ee eeeeeeeeeee eeeeee ee eeeeeeeee eeeeeeeeeeee ee eeeeeee ee eee eee ee eeeeeeeeee. Meee eee eeeeeeee eeee ee eeee eeeeeeee eeeeeeee eee eee eeeeeeeee ee eeee eeeeeeee ee eeeeeeee ee Meeeeee 8.8.8.8.8.

References


Cookie-Einstellungen