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
8.2.14.6.4 Variation 4: Oppolzer's Chiral Sultams

DOI: 10.1055/sos-SD-008-01065

Juaristi, E.; Muñoz-Muñiz, O.; Melgar-Fernández, R.Science of Synthesis, (200681280.

A further example of sodium enolate alkylation controlled by a chiral auxiliary involves the use of sultams that are readily prepared from 10-camphorsulfonyl chloride.[‌68‌,‌69‌] Because both enantiomers of this acid chloride are commercially available, both enantiomers of the chiral sultam are equally accessible. Acyl derivatives such as 82 can be prepared by treatment of sultam 81 with an acyl chloride in the presence of a base (Scheme 33).

Meeeeeeee ee eee eeeeeeee eeeeeee 88 eeee eeeeee eeeeeeeeeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeeeee eeeeeeee, eeeee eeeeeeeee eee eeeeeeeeee eeee eee eeeeeeee eeeeeeeee 88. Meeeeeeeee ee eee eeeeeeee eeeee eeeee eeee eee eeeee eeee, ee eee eeeee eeee ee eeeeeeee ee eee eeeeee eeeeee ee eee eeeeeeeee eeeeee; eeee eeeee eee eeeeeeeeeeeee α-eeeeeeeee eeeeee 88.[‌88‌] Meee eeeeeeeeeeeeeeeeeeeeee eee eeeeeeee ee e eeeeee ee eeeeeeee eeeeeeeee eeee eeeeeeeeee eeeeeeee. Mee eeeeeeeee eee ee eeeeeee ee eeeeeeeeee ee eeeeeee ee eeeeeeeee eeeeeeeeee eeee 88, ee ee eeeeeeeee eeee eeeeeee eeeeeeee eeeeeee ee eeee ee eeeeeee 88.[‌88‌,‌88‌] Me eeeeeee eeee ee e eeee ee eeeeeeeeeeeeee eeeeee eeeeeeee.

Meeeee 88 Mee Mee ee Meeeeeee'e Meeeee Meeeeee ee Meeeeeeeeeeeeee Meeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeeee,e (%) ee 88 eee (%) ee 88 Meeeee,e (%) ee 88 eee,e (%) ee 88 Mee
Me Me 888 88.8 88 88.8 [‌88‌]
Me MM8MM=MM8 88 88.8 88 88.8 [‌88‌]
Me MM8MM8e-Me e.e. 88.8 88 >88 [‌88‌]
Me MM8MMeMeee e.e. 88.8 88 >88 [‌88‌]
Me MM8MMee e.e. 88 88 >88 [‌88‌]
Me (MM8)8eMe 88 88 88 >88 [‌88‌]
Me Me 88 88.8 88 88.8 [‌88‌]
MMe Me 88 88.8 e.e. e.e. [‌88‌]

e Meeee eeeeeee.

e e.e.=eee eeeeeeee.

e Meeeeeeeeeeeee eeeeeee.

e Meeeeee MMMM.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeee Meeee 88; Meeeeee Meeeeeeee:[‌88‌]

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

MMMMMMM: Meeeee eeeeeeeeeeeeeeeeeeeeee eeeeee eeeeeeeee eeee eeeee, eeeeeeeeee eeeeeeeeeeeeeeeeeeee eee, eeeeeeeeeee, eeeeeee.

M eeeeeee ee eeeeee 88 (8.8e, 88eeee), Me8M (88eM, 88eeee), eee MM8Me8 (88eM) ee 8°M eee eeeeeee eeee M8MM8MMMe (88eeee) ee MM8Me8 (88eM) eee eee eeeeeee eee eeeeeee eee 8e. Meeeee eee eeeeeeeeeeeeeee (eeeeee/Me8M) eeee eee M-eeee eeeeee 88 ee eeee eeeee.

M eeee ee eeeeee 88 (8.88eeee) ee MMM eee eeeee ee e 8.8M eeee ee MeMMMM ee MMM (8.88eM, 8.88eeee) eeee 8.8e ee 88°M. Mee eeeeeee eee eeeeeee eee 8.8e, eeee eeeeeee eeee M8M (8.88eeee), eee eeeeeee eee e eeeeeee 8.8e ee 88°M, eeeeee eee eeeeeeee eee eeeeeeee eeee eee. ee MM8Me. Meeeee, eeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8), eee eeeeeeeeeeeeeee (MeMM) eeee eee eeeeeeeee eeeeeee 88.

88% ee M8M8 (88μM, 8.88eeee) eee MeMMM8M (88.8ee, 8.88eeee) eeee eeeee ee 8°M ee e eeee ee 88 (8.88eeee) ee MMM/M8M (8:8, 8eM) eee eee eeeeeee eee eeeeeee ee 8°M eee 8e. Mee eeeeeee eeeee eee eeeeeeeee ee eM8.8 (MMe) eee eeee eeeeeeeee eeee Me8M. Mee eeeeeeee eeee eeeee eee eeeeeee eeee ee eeeeee ee MM8M8. Meeeeeeeeee eee eeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8) eeee eee eeeeee eeeee ee eee eeeeeeeeee eeee 88.

References


Cookie-Einstellungen