Aldol Reactions by Rainer Mahrwald

By Rainer Mahrwald

Aldol Reactions presents a complete up to date review of aldol reactions together with software of alternative steel enolates; catalytic aldol additions catalyzed by means of various 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 proven by way of 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 usual items are mentioned. nice significance is determined to the various chances of the guide of aldol response to put in required configurations in advanced usual product synthesis.

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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. On the other hand, benzyloxyacetaldehyde realizes its chelate potential via pseudo-axial orientation of the benzyl ether (transition state model C). An identical arrangement leads to the selectivity observed with a more highly functionalized aldehyde (entry 4). Perhaps the highly activated nature of the aldehyde in entry 6 leads to a less rigid transition state and thus loss of stereochemical induction.

8 1. TiCl4, amine O 2. 10 Only a few examples of anti-selective titanium-mediated aldol additions have been published. 15 These results are consistent with those obtained in the lithium enolate series. 5. 5 Aldol additions of trisubstituted titanium enolates 42 2 Aldol Reactions with Preformed Enolates A further example of deployment of trisubstituted titanium enolates is the total synthesis of zaragozic acid. 6). The latter could be reacted with 1. Ti(Oi-Pr)Cl3 O 2. 4 Titanium Enolates 43 several carbonyl compounds (aldehydes and ketoesters).

It causes side reactions, such as the reduction of aldehydes. 7 They were able to elaborate a synthesis of crystalline bis-(hexamethyldisilazido)magnesium. Moreover, they were also able to isolate a magnesium intermediate from the self aldol addition of methyl tert-butyl ketone. The structure of this intermediate was determined by x-ray structure analysis. 8 But even the application of magnesium amides caused disadvantages like reduction of aldehydes as one can see by low yields in the enolizable aldehyde series.

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