Stereochemistry reactivity and

Many biofunctional molecules are chiral and nonracemic. It is therefore important to know the relationship between stereochemistry and reactivity. Let us examine the following two examples. 

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A very important relationship between stereochemistry and reactivity arises in the case of reaction at an 5 carbon adjacent to a chiral center. Using nucleophilic addition to the carbonyl group as an example, it can be seen that two diastereomeric products are possible. The stereoselectivity and predictability of such reactions are important in controlling stereochemistry in synthesis. 

DePuy, C. H. Stereochemistry and Reactivity in Cyclopropane Ring-Cleavage by Electrophiles. 40, 73-101 (1973). 

Vogel P. in "Stereochemistry and Reactivity of Sytems Containing n-Electrons", Watson, W.H., Ed. Verlag Chemie International Deerfield Beach, FL, 1983 "Methods in Stereochemical Analysis", pp 147-195. 

The methylene groups at positions 3 and 6 of piperazine-2,5-diones are known to undergo facile condensation with aldehydes to form the corresponding a,/3-unsaturated amides. Two earlier reviews have dealt with this subject. (75FOR51 80FOR251). The review by Sammes covers the literature to 1972 on the synthesis, stereochemistry, and reactivity of... 

The stereochemistry and reactivity of sulfur ylides with 5-substituted adamantan-2-ones has been reported in different solvents.54 The electronic perturbative effect of substituents was found to depend on the solvent and reactant. 

Delfino, A. B., and Buchs, A. Mass Spectra and Computers, 39 109-137 (1973) DePuy, C. H. Stereochemistry and Reactivity in Cyclopropane Ring-Cleavage by Electrophiles. 40, 73-101 (1973) Dimroth, K. Delocalized Phosphorus-Carbon Double Bonds. Phosphamethin-cyanines, X3-Phosphorins and 5-Phos-phorins. 38,1—150 (1973)... 

VogelP (1983) in Watson WH (ed) Stereochemistry and reactivity of systems containing n-electrons. Verlag Chemie, Deerfield Beach, Florida, pp 147-201... 

Small Organosilicon Molecules -Synthesis, Stereochemistry, and Reactivity... 

Two characteristic structural and bonding features of the chlorine and bromine compounds of selenium(IV), in which the role of the inert pair determines much of stereochemistry and reactive properties of the entire class of compounds, are already evident in the simple binary halides. 

Stereochemistry and Reactivity in Cyclopropane Ring-Cleavage by Electrophiles... 

W. Adam, N. Carballeira, O. De Lucchi and K. Hill, in Stereochemistry and Reactivity of Systems Containing ir-Electrons , ed. W. H. Watson, Verlag Chemie, Weinheim, 1983, p. 241. 

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