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By Rainer Mahrwald

ISBN-10: 9048179580

ISBN-13: 9789048179589

Aldol Reactions presents a entire up to date evaluate of aldol reactions together with software of alternative steel enolates; catalytic aldol additions catalyzed through assorted Lewis acids and Lewis bases; enantioselective direct aldol additions; antibodies and enzyme catalyzed aldol additions and the new competitive improvement of organocatalyzed aldol additions. the ability of every approach is verified via numerous purposes in overall synthesis of traditional items. the professionals and cons of those methodologies with reference to stereoselectivity, regioselectivity and alertness in overall synthesis of common items are mentioned. nice significance is determined to the various chances of the guide of aldol response to put in required configurations in advanced normal product synthesis.

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7,8,9 After these initial reports the attention was drawn to the stereoselective execution of this method. The aldol addition proceeds via a chair-like, six-membered transition state, which is more rigid than those of alkali metal enolates. This is due to the shorter boron oxygen bond length, which guarantees a maximum of 1,3-diaxial interactions (R3 ↔ L) and thus the formation of the more stable transition states A and B. For that reason higher stereoselectivities were observed when used with boron enolates, compared to aldol additions of corresponding lithium enolates.

Oppolzer W (1988) Pure Appl Chem 60:39 34. Evans DA, Takacs JM, McGee LR, Ennis MD, Mathre DJ, Bartroli J (1981) Pure Appl Chem 53:1109 35. Evans DA (1982) Aldrichimica Acta 15:23 36. Braun M (1981) Angew Chem Int Ed Engl 26:24 37. Inoue T, Liu JF, Buske DC, Abiko A (2002) J Org Chem 67:5250 38. Fanjul S, Hulme AN, White JW (2006) Org Lett 8:4219 39. Evans DA, Sjorgren EB, Bartroli J, Dow RL (1986) Tetrahedron Lett 27:4957 40. Evans DA, Dow RL, Shih TL, Takacs JM, Zahler R (1990) J Am Chem Soc 112:5290 41.

24 The same is true for the generation of defined boron enolates of carboxylic esters. (E)-boron enolates of carboxylic esters were obtained when used with tert-butyl esters and dicyclohexylboron triflates in the presence of triethylamine selectively. 25 As pointed out in the introduction there exist in general three different ways for an asymmetric execution of aldol reactions. Conventional chiral enolates have been used for this purpose extensively. Several chiral auxiliaries have been developed to achieve this aim.

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Aldol Reactions by Rainer Mahrwald

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