Science of Synthesis

Wessjohann, L. A.; Kaluđerović, G. N.; Neves Filho, R. A. W.; Morejon, M. C.; Lemanski, G.; Ziegler, T., Science of Synthesis: Multicomponent Reactions, (2014) 1, 473.

Controlling the stereoselectivity of Ugi reactions is still a general problem because the selectivity is often very low. This fact has led to the development of some effective stereoselective Ugi reactions in recent years.[‌161‌] One way to achieve stereoinduction in Ugi four-component reactions is the use of chiral amines. Kunz and co-workers[‌30‌–‌33‌] and Ugi and co-workers[‌35‌–‌37‌] have used various glycosylamines as chiral auxiliaries in Ugi four-component reactions using zinc(II) chloride as catalyst, resulting in excellent diastereoselectivities and good yields. High diastereomeric ratios with an R configuration of the newly formed amino acid amide are obtained with d-galactosyl- or d-glucosylamine derivatives (‌Scheme 52‌).[‌30‌] For the synthesis of the corresponding Ugi products in which the newly formed amino acid amide moiety has S configuration, l-arabinosylamine derivatives were used as the chiral amine component (‌Scheme 53‌).[‌33‌]

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‌Meeeee 88‌ Meeeeeeeeeeeeeeeee Mee Meeeeeeee ee M-Meeeeeeeeeeeeee Meee Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

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‌Meeeeeeeeee 88‌

M8	eee	Meeee (%)	Mee
Me	>88.8:8.8	88	[‌888‌]
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e Meeeeeeeee ee MMM.

Meeeeeee, Mee eee ee-eeeeeee[‌888‌,‌888‌] eeee eeeeeeeeeeee eeeeeee eeeeee eeeeee eeeeee eee eeeeeeeeeeeeeee Mee eeeee-eeeeeeeee eeeeeeeee eeeeee 8-eeeeeeeeeeeee-8-eeeeeeeeeeee ‌888‌ eeee eeee eeeeeeeeeeeeee eeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeee 8-Meeeeeeeeeeee-8-eeeeeeeeeee Meeeeeeeeee ee Mee Meeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meee eee ee-eeeeeee[‌88‌,‌888‌] eeee eeeeeeeee e eeeeeeeee Mee-eeee eeeeeeee ee α-eeeeeeeeeeeeeeeeee eee e eeeeee eeeeee eeeee ee eeee eeeeee 8-eeeeeeeeeeeeeeeee-8-eee eeeeeeeeeee (‌Meeeee 88‌). Me eee eeeeeeee ee eeeeeeeeeeeeeeee eeee eee 8,8,8-eeeeeeeeeeeeeeee ee eee eeeeeee, eeee eee eeeeee eeeeee ee eeeeeee ‌888‌ ee eeeeeeee ee eeee eeeee.

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeeeeeeeee-8-eee Meeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeee ee eee eeeeeeeeeeeeeeeeeeeeee eee eeee ee eeeeeeee ee eeeeeee eeeee[‌888‌] ee eeee eeeeee eeeeeeeeeeeeeeeeeeeee.[‌888‌–‌888‌] Meeeeeeee, eeeeee eeeeeeeee eeee eeee eee eeeeeeeeeeeee Mee eeeeeeee ee eeeeeeee eeeeeeeeeeeeee eeeeee.[‌888‌] Mee eee ee-eeeeeee[‌888‌] eeeeeeee eeeeeeee ee eeeeeeeeeeeeeeee Mee eeeeeeee eeeee eeeeeeeeeeeeeeee eee e eeeee eeeeeeeeee eeee eeeeeee e eeeeee eeeeeeeeee eeeeee, eeee ee (M)-8,8′-eee(8,8,8-eeeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeeeeee-8,8′-eeee, eee eee eeeeeeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeee ‌888‌ ee eeee eeeeee eee eeee eeeeeeeee eeeeeeeeeeee eeeeee eeeeee (‌Meeeee 88‌). Meeeee eeeeeeeeeee eeeee eeee eeee eeeeeeee eeee eeeee ee eeeeeeee eee eeeeeeeeee Mee-eeee eeeeeeeee eeee eeeeeeeeee eeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeeeeeeeee Meeeeeeee ee Meeeeee Meeeeeeeeee ee Mee Meeeeeee[‌888‌]

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Meeeeeeeeeee Meeeeeeee

M-eeee-Meeee-8-(M-eeeeeeeeeeeeeeeee)eeeeeeeeeee ‌888‌ eee ‌888‌; Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eee eeeeeeeeeeeee (8.8 eeee), eee eeeeeeee (8.8 eeee), eeeeee eeee (8.8 eeee), eee eeee-eeeee eeeeeeeeee (8.8 eeee), eeeeee ee −88 °M, 8.8 M MeMe8•eMMe8 (8 eeee) ee MM8Me8 eee eeeee. Meeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeee (MMM), eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeee ee MM8Me8 (88 eM), eee eee eeee eee eeeeee eeee eee. ee MeMMM8 eee M8M eee eeeee (MeMM8). Meeeeeeeeeeeeeeee ee eeeee eeeeeeeeeeeeee eeeeeeeee eee eeee eeeeeeee.

M-(8-Meeeee-8-{[(M)-8-(8-eeeeee-8,8,8-eeeeeeeeeeeee[8.8.8]eeeee-8-ee)eeeee]eeeee}-8-eeeeeeeee-8-ee)-M-[(M)-8-eeeeeeeeeee]eeeeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

M eeee ee eeeeeee (8–8 eeee), eee eeeee (8 eeee), eee eeee (8 eeee), eee eeeeeeeeee ‌888‌ (8 eeee) ee MeMM (8 eM) eee eeee eee 8–8 e. Meee, eee eeeeeee eee eeeeeeeeeeee eeee eeeeee eee (e eee eeeee ee Me8M eee ee eeeee ee eeeeeee eeeeeee ee eee eeeee eeeee, eee eeee ee eee eeeeeeee) eee eeeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8 ee 8:8 eeeeeeee).

(8M,8M)-8-Meee-8-eeeee-M-eeee-eeeee-8-eee-8-eeeeeeeeeeeeeeee-8-eeeeeeeeeeee ‌888‌; Meeeeee Meeeeeeee:[‌888‌]

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References