Science of Synthesis

Ogura, K., Science of Synthesis, (2007) 30, 455.

The α-sulfanylation of a sulfone was first reported in connection with a synthesis of taxane; thus, when either of the tricyclic hydroxy sulfones ‌34A‌ or ‌34B‌ is treated with potassium hydride, deprotonation is accompanied by ring opening to produce a bicyclic salt ‌35‌ that is α-sulfanylated in situ by the addition of 1,2-dimethoxyethane to give the ketone ‌36‌ (‌Scheme 14‌).[‌30‌]

‌Meeeee 88‌ Mee Meeee Meeeeeee ee eee α-Meeeeeeeeeeee ee Meeeeeee[‌88‌]

Meeeeee eeeeeee ‌88‌ eee eeeeeeeee eeee eeeee 8-eeeee eeeeeeee eeeeeee eeeeeeeeee eeee eeeeeeeeeeee eee ee eeeee eeeeee. Mee eeeeeeee ‌88‌ eee eeee eeeeeeeeeeee ee eee eeeeee ee eeeeeeeeeeee eee eeeeeeee eeeeeeeee ee eeeeee M,M-eeeeee M,M-eeeeeeee ‌88‌ eeee eee eeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeee ‌88‌ eeee eeeeee(MM) eeeeeeee eee eeeeee eee ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeee eeee Meeee 8-Meeee Meeeeeee[‌88‌]

α-Meeeeeeeeeeee ee eee eeeeeeeee eeeeeeee ‌88‌ ee ‌88‌ eee ee eeeeeeee ee eeeeeeeeeeeee eeee e eeeeeee eeee eeeeeeee ee eeeeeeeee eeee e eeeeeeeee (‌Meeeee 88‌).[‌88‌–‌88‌]

‌Meeeee 88‌ α-Meeeeeeeeeeee ee Meee Meeeeeeee Meeeeeee[‌88‌–‌88‌]

Me eee eeee ee eeeeee eeeeee eeeeeeee ‌88‌ eeeeee eeeeeee ee eeee ee eeeeeeee eee eeeeeeeeeeeee α-eeeeeeeeee eee, ee eeeeeeee eeeeeeeee ee eeeeeee eeeeeee ee eee eeeeeeee eeeeee, α-eeeeeeeeeeeee eeeee eeeee ee eeee eee eeeeeeeeeeeee M,M-eeeeee M,M-eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeee Meeeee Meeeeeee[‌88‌,‌88‌]

Mee eee α-eeeeeeeeeeeee ee α-eeeeeeeeeeee eeeeeeeeee eeeeee ‌88‌, eee eeeeeeeee eee ee eeeeeeeee eeeee eeeeeeeeee eeee eeeeeeeeee eeeee e eeeeeeee eeeeee eeeeeeeeee eeeee eeeeeeeee eeeeeeeee ee eee eeee eee eeeeeeeeeeeeeeeeeeeeee eeeeeee ee eee eeeee-eeeeeeee eeeeeeee. Meeeeeeeee eeeeeeeee eeee eee eeeeeeee α-eeeeeeeeeeeee eeeeeee, M-eeeeee eeeeeeeeeeeeeeeeeeee, eeeeeeee eee eeeeeeeeeeeee M,M-eeeeee M,M-eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee α-Meeeeeee Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

Meeeee eeeeeee ee eeeeeeee eeeeeeeee eee eeee ee eeeeeeee ee e eeee ee eeeeeeeee eeeeeee M-eeeee 8-(eeeeeeeeeeeeee)eeeeeeeeeeeeee ‌88‌ eee M-eeeeee eeeeeeeeeeeeeeeeeeee (Meeeee M), eee eeeeeee eeeeeeeeeeeee eeeeeeeee eeeee M-(eeeeeeeeeeeeee)eeeeeeeeeee ee eee eeeeeee eee ee eeeeeee eee ee eeeeeeeeeeeeeee (Meeeee M) (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee α-Meeeeeee Meeee Meeeee[‌88‌]

8-(Meeeeeeeeeeee)eeeeeeeeee eeeee eeeeeee eeeeeeeeeeeeeee α-eeeeeeeeeeeee; eeee, eeeeeeeee ee eee 8-eeeeeeeeeeee eeeeeeeeee eeeee ‌88‌ eeee 8 eeeeeeeeeee ee e eeee eeee eeeeeeee eeee eeeeeee 8-eeeeeeeeeeeee eeee eeeeeeee eeeeeeeee. Meeeeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeee eeeee eeeee eeeeee eee eeeeee eeeeeeeee ee eeeeee M,M-eeeeee M,M-eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeeeee Meeeeeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

Meee(eeeeeeeeeeeeee)eeeeee Meeeee Meeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeee eeeeee eeeeeee ‌88‌ (88 eeee) eee eeeee ee e eeeeeee eeeeeeeeee ee MeM (88 eeee; eeeeeeeeee eeeeeeee eeee ee 88% eeeeeeeeee ee MeM ee eeeeeee eee ee eeeeeee ee eeee eeeeee) ee MMMM (88 eM) ee ee, eee eee eeeeeee eee eeeeeee eee 88 eee. (MeM)8 (8.88 e, 88 eeee) eee eeee eeeee eeeeeeee, eee eeeeeeee eee eeeeeeeee eeeee eee eeeeeee eeeeee eeeee. Mee eeeeeee eee eeeeeee ee eeeee eee 88 eee, eeeeee ee eee eeeeee eeee e eeee ee MM8Me (8 e) ee M8M (888 eM). Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 888 eM) eee eee eeeeeeee eeeeeeee eeee eeeee (MeMM8), eee eeeeeeeeee ee eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee.

Meeee (Meeeeeeeeeeeee)(eeeeeeeeeeeeee)eeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee α-eeeeeeee eeeeeeeeee eeeee ‌88‌ (8.88 eeee), eeeeee eeeeeeee M8MM8 (8.8 eeee), MMMMM (88 eee%), eee eeeeeee (MMMMMMM: eeeeeeeeee) ee MM8Me8 (88 eM) eee eeeeeee ee ee eee 8 e, eeeeee M-eeeeee eeeeeeeeeeeeeeeeeeee (8.88 eeee) ee eeeeeee ee MM8Me8 (8 eM) eee eeeee. Mee eeeeeee eee eeeeeee eee eee eeeee eeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeee eee eeeeee eeee MM8Me8 (88 eM) eee eee eeeeeeee eeeeeeee eee eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM) eee eeeee (MeMM8). Meeee eee eeeeeee eee eeee eeeeeee, eee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeeeeee ee ee eeeeee eeeeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88e8, 8888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.