By Rainer Mahrwald
Aldol Reactions presents a accomplished updated evaluate of aldol reactions together with program of other steel enolates; catalytic aldol additions catalyzed by way of varied Lewis acids and Lewis bases; enantioselective direct aldol additions; antibodies and enzyme catalyzed aldol additions and the hot competitive improvement of organocatalyzed aldol additions. the ability of every process is established by means of a number of functions in overall synthesis of ordinary items. the professionals and cons of those methodologies with reference to stereoselectivity, regioselectivity and alertness in overall synthesis of traditional items are mentioned. nice value is determined to the various chances of the handbook of aldol response to put in required configurations in complex traditional product synthesis.
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Evans DA, Starr JT (2004) Angew Chem Int Ed 41:1787 69. Loh TP, Feng LC (2001) Tetrahedron Lett 42:6001 70. Jiang Y, Hong J, Burke SD (2004) Org Lett 6:1445 71. (a) Paterson I, Tudge M (2003) Angew Chem Int Ed 42:343; (b) Paterson I, Tudge M (2003) Tetrahedron 59:6833 72. Zou B, Wie J, Cai G, Ma D (2003) Org Lett 5:3503 73. Chen J, Forsyth CJF (2003) J Am Chem Soc 125:8734 74. 4 Titanium Enolates Titanium enolate-based aldol additions have a tremendous synthetic potential. 3 The titanium enolates were generated mostly by transmetallation of corresponding lithium enolates with ClTi(Oi-Pr)3 or ClTi(NR2)3.
6). The latter could be reacted with 1. Ti(Oi-Pr)Cl3 O 2. 4 Titanium Enolates 43 several carbonyl compounds (aldehydes and ketoesters). 6 may be rationalized by invoking the proposed transition state model (Fig. 1). The chair-like transition state A orients the α-ketoester on the face of the tartrate enolate opposite to the tert-butyl ester. Thus, the methyl ester of the electrophile occupies a pseudo-axial orientation allowing chelation to titanium. The stereoinduction observed for unfunctionalized aldehydes (entries 1 and 2) can be rationalized by a pseudo-equatorial orientation of alkyl or aryl groups in the closed transition state model B.
14). 4 Titanium Enolates 49 O O O OH X O O O O 1. Et3N 2. i-Pr2 NEt 3. 44 For the development and application of chiral oxadiazinones in enantioselective titanium enolate aldol reactions see Casper et al. 45 Chiral titanium(IV) alkoxides were used for the synthesis of optically active β-hydroxy ketones. Duthaler and coworkers generated chiral titanium enolates by transmetallation of lithium enolates of propionate with CpTi(OR2)2Cl (R2: 1, 2:5,6-di-O-isopropylidene-α-d-glucofuranose). 47,48,49,50,51 Some spectacular examples are illustrated in the following schemes in order to demonstrate the power and selectivity of these transformations.
Aldol Reactions by Rainer Mahrwald