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
36.10.1.1.6 Method 6: Aziridine Substitution Reactions

DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (200836992.

The hydrolytic ring opening of aziridines 37 can be achieved under a range of conditions to afford β-amino alcohols with both stereo- and regiocontrol (e.g., conversion of 38 into 39, Scheme 17).[‌121‌,‌122‌] The regio- and stereoselectivities are determined by the nature of the protecting group on the nitrogen atom, the stereochemistry of the aziridine starting material, and the presence of neighboring functionality.

Meeeeeeee eeeeeeeeee, eeee ee M-eeeeeeeeeeeeeee, eee ee eeee eeeeee eeeee eeeeeeeeee eeee eeeeeeeeee, eee eeeeeee eeeee eeeee eeee eeeeeeee eeeeee(MM) eeeeeee[‌888‌,‌888‌] ee eeeeeeeeeeeeeeeeee eeeeeeeee[‌888‌] ee e eeeeeeee. (8-Meeeeeeeeeeeeee)eeeeeeeee (e.e., 88, M8=Me; M8=M; M8=MM8MM; M8=Me; M8=M) eee eeeeeee e eee-eee eee-Meeee eeeeeeeeeeeee eee eeeeeee eeee-eeeeeee eeeeeeee eeee eeeee-eeeee eeeeeeee ee eeee eeeeeeeeeeeeeeeeee eeee β-eeeee eeeeeeee ee eeeeeeeee eeeeee.[‌888‌‌888‌]

Mee eeeeeeeeee eeee eeeeeee ee eeeeeeeeeeee eeeeeeeeee ee eeeeeee eeeeeeeee eeeee eeeeee eeeeeeeeee eee eeeeeeee eeee-eeeeeee eeeeeeeeee. Mee eeee eeeeeee ee eeeeeeeeeeeeeee eeee ee eeeeee eeeeeeeeeee eeeeeeeee eeeeee eeeeeeeeeeeeeeee ee eee eeeeeee eeeeeeee;[‌888‌,‌888‌,‌888‌] eee eeeeeeeeeeeeeeeee ee eee eeeeeeee eee ee eeeee ee eeeee ee e eeeeeeee eeeeee ee eeeeeeee eeeeeeeeee ee eeeeee eeeeee eee eee- ee eeee-β-eeeee eeeeeee. Meeeeeeee ee eee eee-eeeeeee eee ee eeeeeeeeeeee ee eeeee ee ee MMe eeeeeeeee; eeeeeeeeeeeeee eeeeee ee eee eeeeee ee eee 8-eeeeeeeeeeeee eeeeeee ee eeeeeeeeeeee eeeeeeeeeeeeee, eeeee ee eeeeeeeeee ee eeeeeee eee eee-β-eeeee eeeeeee.[‌888‌,‌888‌,‌888‌]

Mee eeeeee eee eeeeeeeeeeeeee ee eee eeee eeeeeee ee eeeeeeeeeeee 8-(8-eeeeeeeeee)eeeeeeeeee eee eeee ee eeeeeeeeee ee e eeeeeeee eeeeee ee eeeeeeee eeeeeeeeee; eeee 8-eeeeeeeeeeeeeee eeee eeeeeeeee eeee eeeeeee ee eeeeeeeee 88 eeeeeee eee β-eeeee eeeeeee 88, eeeeeee Meeee eeee eeeeeeeee eeee eeeeeee eeee eeeee eeeeeeeeeeeeeeeeee eeeee eeeeeee eeeee eee eeeeeeeeeee eeeeeeeeeee 88 eeee eeeeeee eeeeeeeee ee eeeeeeeeeeeeeee ee eee 8-eeeeeeee.[‌888‌] Mee eeeeeeeeeee ee eee eeeeee eeeeeeee eee ee eeeeeeeee ee eeeee ee eeeeeeeeeee-eeeee eeeeeeeeeeeee; eeeeee, eeeeee eeeeeee ee eeeeeeeeeee eeeeeeeeee eeeeee eee ee eeeeeeee ee eeeeeee eeeeeeee ee eeeeeeeee-eeee-eeeeeee eeeeeeeee eeee eeeeee eeeeeeeeeeee.[‌88‌,‌888‌]

Meeeee 88 Meeeeeeee-Meee-Meeeeee Meeeeeeee Me Meeeee β-Meeee Meeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌]

Meeeeeeeeee 88

Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8. Me8M (8.8 eeeee), Me8M (8 eeeee), MMMM (eee.), MM8Me8, 88°M, 88eee
8. MM8MMe8 (8 eeeee), MMM, 88°M, 8.8e
8. M8M, ee, 8e
88 [‌888‌]
ee MMeM8 (8 eeeee), MMM/M8M, 88°M, 8e 88 [‌888‌]
MeMM (8 eeeee), MeMM/M8M (8:8), ee 88 [‌888‌]
8. MM8MMe8 (8 eeeee), MeMM, eeeeee, 8e
8. ee MeMMM8
88 [‌888‌]
MeMM, M8M 88 [‌888‌]
8. MM (8 eeeee), MMM, 8°M, 8e
8. Me8Me(MM)Me8 (8 eeeee)
88 [‌888‌]
Me8MMMM8 (8.8 eeeee), M8M, 88°M 88 [‌888‌]
MMM (8.8 eeeee), M8M/MeMM (8:88) 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M)-8-Meeee-8-eeeeeeeee-8-ee-8-ee (88); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeeeeeee eeeeeeeee eeeeeeeeee eeee (8888%) eee eeeee eeeeeeeeeee ee eeeeeeeee eeee e eeeee ee eeeeeee eee eeeeeeeee eeeeeeeeee eee ee eeeeeeeee eeeeeeeeeee ee eee eeeeeee.

MMeM8 (88 μM, 8.888eeee) eee eeeee ee e eeee ee eeeeeeeee 88 (88.8ee, 8.888eeee) ee MMM (8eM) eee M8M (8.8eM), eee eee eeee eee eeeeee ee 88°M eee 8e. M8MM8 eee eeeee eee eee eeeeeee eee eeeeeee eee 88eee, eeee eeeeeeee, eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/MeMM 88:8, 8% MM8MM) ee e eee-eeeeeee eeeee; eeeee: 88.8ee (88%); [α]M88 88.8 (e 8.88, MM8Me8).

References


Cookie-Einstellungen