Mukaiyama TADDOL-catalyzed

Table 6.45 Taddol-catalyzed Mukaiyama aldol reactions of N,Q-acetals.

Taddol-Catalyzed Mukaiyama Aldol Reactions of Aldehydes [7] (p. 245)... 

Mukaiyama T, Inubushi A, Suda S, Kara R, Kobayashi S (1990) Chem Lett 1015 Substituted aromatic solvents have been shown to have a dramamtic effect on the enan-tioselectivity of Ti TADDOL-catalyzed Diels Alder addition reactions, see Narasaka K, Iwasawa N, Inoue M, Yamada T, Nakashima M, Sugimori J (1989) J Am Chem Soc 111 5340... 

The first examples of the hydrogen-bond-promoted enantioselective Mukaiyama aldol condensation involving 1-acylphosphonates (472) has been described by Rawal and co-workers. These reactions were catalyzed by commercially available Taddol (474) (a,a,a ,a -tetraaryl-l,3-dioxolane-4,5-dimethanol) and proceeded in good yield and excellent diastereo- and enantioselectivity. This mild and general method produced phosphonates (473) with two chiral centers, one tertiary and one quaternary (Scheme 120). 

Scheme 1.28 Enantioselective vinylogous Mukaiyama aldol reactions catalyzed by TADDOL (22a).

Scheme 10.2 Enantioselective vinylogous Mukaiyama aldol reaction catalyzed by taddol 1.

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