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Aldol Reactions by Rainer Mahrwald

By Rainer Mahrwald

Aldol Reactions offers a accomplished updated review of aldol reactions including:

  • Application of other steel enolates
  • Catalytic aldol additions catalyzed through diversified Lewis acids and Lewis bases
  • Enantioselective direct aldol additions
  • Antibodies and enzyme catalyzed aldol additions
  • The fresh competitive improvement of organocatalyzed aldol additions.

The energy of every approach is proven via a number of purposes in overall synthesis of normal items. the professionals and cons of those methodologies in regards to stereoselectivity, regioselectivity and alertness in overall synthesis of average items are mentioned. nice value is determined to the varied chances of the handbook of aldol response to put in required configurations in advanced typical product synthesis.

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Evans DA, Burch JD, Hu E, Jaeschke G (2008) Tetrahedron 64:4671 67. Evans DA, Siska SJ, Cee VJ (2003) Angew Chem Int Ed 42:1761 68. 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.

20 Total synthesis of callystatin A procedure. The reaction with (S)-2-methylbutanal 52 yielded the syn-aldol adduct 53 with 98% selectivity. Chain elongation was then performed by the same method, a second aldol addition of the chiral aldehyde 54 with the chiral titanium enolate of 55. The final stereopentad 56 was isolated with 98% selectivity. 64 Four years later, the Crimmins group published the total synthesis of spongistatin, employing the same conditions as described above. 65,66,67 Chakraborty and coworkers developed a total synthesis of crocacin using the Crimmins’ procedure in initial aldol steps.

TiCl4, 2. 5 equiv (–)-sparteine, 3. R1-CHO Method B: 1. 0 equiv. TiCl4, 2. 1 equiv i-Pr2NEt, 3. 12 Oxazolidinethione-based syn-selective aldol additions O O 1. TiCl4 2. i-Pr2NEt 3. r. r. = 95:5 O CO2Me N i-Pr R N O i-Pr O CO2Et 1. TiCl4 2. R-CHO 3. r. r. 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.

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