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20.2.13.1.3.1 Method 1: Addition to α,β-Unsaturated Acids

DOI: 10.1055/sos-SD-020-00571

Sartori, G.; Maggi, R.Science of Synthesis, (200720593.

α,β-Unsaturated carboxylic acid sodium salts 55 can be converted into 2-hydroxy-3-(tosylamino)alkanoic acids 56 with high levels of regioselectivity by reaction with chloramine-T trihydrate (sodium chlorotosylamide) and 0.2mol% of dipotassium osmate.[‌50‌]

Meeeee 88 Meeeeeeeeee ee 8-Meeeeee-8-(eeeeeeeeee)eeeeeeee Meeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meee (e) Meeee (88/88) Meeee (%) Mee
M M 8 8:8 88 [‌88‌]
M Me 8 8:8 88 [‌88‌]
MM8M M 8 88 [‌88‌]
Me M 88 8:8 88 [‌88‌]
8-MeM8M8 M 88 8:8 88 [‌88‌]
8-M8MM8M8 M 88 8:8 88 [‌88‌]
M8M8 M 8 8:8 88 [‌88‌]
8-eeeeeee M 88 8:8 88 [‌88‌]

Mee eeeeeeee eeeeee ee eeeee eee ee eee eeeeeeee ee eeeeee eeeeeeee eeeeeeeee. Meee ee, ee eeeeeeeee, eeee eeeeeee 88 eee 88 eee ee eeeeeeee, eeeeee 88 ee, ee eee eeeee eeeeeeee, eee eeee eeeeeee ee ee eeeee eee eeeee eee (Meeeee 88).

Meeeeeee ee eeeeee ee eeeeeeeeeeeeee eeeeeeee eeeeeeee eee eeeeeeeeeeee eeeeeeeeeeeeee 8-eeeeeeeeeeeeeeee, eeeee eee eeeeeee eeeeeeeee eeee M-eeeeeeeeeee β-eeeee eeeee ee eeeeeeeeee ee eeee eeeeee (8888%). Mee eeeeeee, eeeeeeeeeeeeee eeeeeeee eeeee ee e eeeeeeee ee eeeeeeeeee ee eeeeeeeeee, eeeeee ee 88°M eee 88eeeee eeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeeeeee eeeeeeeeeeeeee eeeee ee 88°M eee 8eeeee eeeee eeeeeeeee eeee 88 ee 88% eeeee (Meeeee 88).[‌88‌] Meee eeeeeeee ee eeeeeeeeeeee eeeeee ee eee eeeeeeeee ee eee eeeeeee eee eeeeeee eee eeeeeeeeeeeee.

Meeeee 88 Meeeeeeeeee ee β-Meeeeeee-Meeeeeeeeee Meeeeeeeee Meeee ee Meeeeee Meeeeeee ee M=M Meeee[‌88‌,‌88‌]

Mee eeeeee eeeeeeeeeeeeeeee eeeeeeeee ee β-eeeee eeeee, e.e. 88, eee ee eeeeeeeeeeee ee eeeeee-Meeeeee eeeeeeee ee (M)- eee (M)-8-(eeeeeeeeeeeee)-8-[(eeeeeeeeeeeeee)eeeee]eeeeeeeeeee ee eeeeee eeeeeee eeeeeeeeeee ee M-eee-8-eeeeeee. Mee eeeeeee, eee eeeeeee eeee ee (M)-8-(eeeeeeeeeeeee)-8-[(eeeeeeeeeeeeee)eeeee]eeeeeeeeeee ee eeeeeeeeeeeeeee ee 88°M eeeeee eeee eeeeee eeee-8-eeeeee eeee 888eeeee ee eeee eee eeeeeeeee eeeee eeeeeeeeeeee ee 88% eeeee (ee 88.8:8.8). Mee eeeeeeeeeeee ee eeeeee ee ee eeeeeeeee ee 8888°M ee eeeee eeeeeeeeee Meeee eeeeee eeeee eeeeeeee eeeeeeee (888888eMe) eeeee eeeeeeee eeeeeeeeee. Me eeeee, eeee eeeeeeee ee eeee eee-eeee eeeeeee eee eeeeeeee; eeeeee eee eee eeeee eeee eee ee eee eeeee 8888%, eeeee eee eeeeee eeee eeeeeeee ee 8888% eeeee. ­Meeeeeeeeeeeee eee eeeeeeeeeeee eeeeee ee eee eeeeeeee ee ee ee 88:8 eee eeeeeeee.[‌88‌]

M eeeeeee eeeeeeee eeeeeeeeeee ee eee eeee eeeeeeee ee eeeeeeeeeee ee eee eeeeeeeeeee ee e eeeeee ee eeeee-8-eeeeeeeeeeeeeeee-8-eeeeeeeeee eeeee ee eeee eeeeeeeeeeeeee eee eeeeeeeeeeee eeeeee (8888% ee, >88% ee). Mee eeeeeeee eeeeeeee ee eee eeeeeeeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee (M)-8-(eeeeeeeeeeeee)-8-[M-(eeeeeeeeeeeeee)eeeee]eeeeeeeeeee ee ω-eeee-eeeeeeeeeee α,β-eeeeeeeeeee eeeeeee 88 eeeeeeee ee eeeeeeeeee Meeeeee-eeee eeee eeeeeee ee eee eeeeeeeeeeee eeeee eeeeee ee eeee (M,M,M)-88. Mee eeeeeeeee ee eeeeeee eeee 88 ee eeeeeeeee MM eeee eeeeeeee, eeeeeeeee eee eeeee eeeeeee (M,M)-88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee eeeee-8-Meeeeeeeeeeeeeee-8-eeeeeeeeee Meeee[‌88‌]

Meeeeeeeeee 88

M8 e M Meeeee (%) ee 88 ee (%) ee 88 ee (%) ee 88 Meeeee (%) ee 88 Mee
Me 8 M 88 [‌88‌]
Me 8 M 88 [‌88‌]
e-Me 8 Me 88 88 >88 88 [‌88‌]
e-Me 8 Me 88 >88 >88 88 [‌88‌]
e-Me 8 M 88 88 >88 88 [‌88‌]

e Meee 88.

e Meee 88.

Meeee eeeeeeeeeeee eee ee eeeeeeee ee eeeeeee eeeeeeeeeee ee ee eeeeeeeeee Meeeeee eeeeeeee (Meeeee 88).[‌88‌] Meee, eee eeeeeeeee eeeee 88 eeeeee eeee (8M,8M)-8,8-eeeeeeee-8-eeeeeeeeeeeeeeeeee-8-eee 88 ee eee eeeeeeeeeeeeeee ee 88°M eeeeee, eeeee eeeeeeeeeeee/eeeeeeeeee, (M)-8-eeeeeeeeeeeee eeee (88% eeeee, 88% ee).

Meeeee 88 Meeeeeeeeee ee (M)-8-Meeeeeeeeeeee Meee[‌88‌]

Mee eeeeeeeeee eeeeeeee ee ee eeeee eeeee ee eee eeeeeeeeeee eeeeeeee eeeeee eeeeeeeee ee e eeee ee Meeeeee eeeeeeeeeeeeeeeeee ee ee eeeeeeee (Meeeee 88).[‌88‌] Mee eeeeee eeeeeeeeeeeee ee 8.8 eeeeeeeeeee ee eee eeeeeee eeeee eeeeeeeeeeee ee eee eeeeeeeeeee eeeeeeeee ee eeeeeeeee ee eeeeee eeeeeeeeeeee eeee e eeeeeeee ee 8,8-eeeee-8-eeeeeeee[8.8]eeeeee ee eeeeeeeeeeeeeee ee 88°M eee eeeeeeee eeee eeeeeeeeeeeeeeeeeeee eeeeeeee eee eeeeeeeeeee 88 eee eeee eeee 8 eeeeeeeeee ee eeeeeeeeeee; eeeeeee ee eee eeeeeeeeeee ee eeeeeee eee ee eeeeeeeeee, eeeee eeeee eee eeeeeeeeeeeee eeeee eeee 88 ee 88% eeeee (>88% ee).

Meeeee 88 Meeeeeeeeee ee (8M,8M)-8-Meeee-8-eeeeee-8,8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeee Meee[‌88‌]

M 8-eeeeeeeeeeeeeeeeeee eeee eee ee eeeeeeeeeee ee eeeeee eeeeeee eeee eeeeeeee ee e eeeeeeee ee eeeeeeee(eeeeee)eeeeeeeee eee e eeeeee eeee-eeeee eeeeeeeeeeeeee eee eeeeeeeee eeee eeeee; 8-[eeeeeee(eeeeee)eeeeeeeeee]eeeeeeeee eeee (88) ee eeeeeeee ee 88% eeeee.[‌88‌] Meeeeeeee, eeee eeeeeeeeeeeeeeeee ee eeeee ee eeeeeee eeee eeeeeee eeee, eee eee eeeeeeeee eeeeeee ee eeeeee ee 88°M eee 8eeeee, eee eeeeeeeeeeee eeeeeee 88 ee eeeeeeee ee 88% eeeee. Meee eeeeeeee ee eeeeeeeee ee eeeee eeee 8-eeeeeeeeeeeeeee eeee eeeeeeeeeee eee eee eeeeeeeee eeeeeee ee eeeeeee ee eeee eeeeeeeeeee eee 88 eeeeeee ee eeeeee eeeeeeee(8-eeeeeeeeeeee)eeeeeeeeeee 8-eeeeeeeeeeeeeeee ee 88% eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee 8-Meeeeeeeee-Meeeeeeeeee Meeeeeeee Meeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeee-8-eeeeee-8-(eeeeeeeeee)eeeeeeeee Meee (88, M8=M; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

8-Meeeeeeeeeeee eeee (88e, 8eee) eee MeMMM8 (888e, 8.8eee) eeee eeeeeeeee ee eee eeeee (8.8M) ee e 8-M Meeeeeeeee eeeee. Meeee eee eeeeeeeee eeeeee, eeeeeeeeee-M eeeeeeeeee (888e, 8eee) eee eeeee, eeeeeeee ee M8[MeM8(MM)8] (8.88e, 8.8 eee%). Mee eeee eeeee eeeee ee eee eeeeeee eee eeeeeeeeeeeeee ee eeee eeeee. Mee eeeeeee eee eeeeeee eee 8e, eeeee eeeee eeee ee eeeeeee eee eeeeee eeeee. Me eeeeeee eeeee ee eeeeeeee ee eeee eeeee eeeee eee eeeeee/eeeeee eeeee eeee. 8M MMe (888eM) eee eeee eeeee, eee eee eeeeeee eee eeee ee eee eeeeeeeeeeee eeeeeeeee. Meeeeeee eeeeee, eee eeee eeeeeeee, eeeeee eeee e eeeee eeeeee ee eeee M8M, eee eeeee; eeeee: 88%.

References


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