Abstract
Based on a Cambridge Structural Database (CSD) search, a meta-analysis of 116 structures of alanine H3NC alpha H(CH3)C '(O)O and its derivatives H3NC alpha H(CH3)C '(O)O(H/R/M), protonated, esterified, or coordinated at the carboxylic group, shows that in the first step of a chirality chain, the L configuration at C-alpha induces (M) and (P) conformations with respect to rotation around the ...
Abstract
Based on a Cambridge Structural Database (CSD) search, a meta-analysis of 116 structures of alanine H3NC alpha H(CH3)C '(O)O and its derivatives H3NC alpha H(CH3)C '(O)O(H/R/M), protonated, esterified, or coordinated at the carboxylic group, shows that in the first step of a chirality chain, the L configuration at C-alpha induces (M) and (P) conformations with respect to rotation around the central C ' C-alpha bond. In the second step, the (M) and (P) conformations selectively distort the planar carboxylic group C alpha C'(O-cis)O-trans to asymmetric flat (R) and (S) tetrahedra. High diastereoselectivities are caused by the two players attraction N horizontal ellipsis O-cis and repulsion O-trans horizontal ellipsis C-Me, which work together in (L,M,R) configurations but against each other in (L,P,S) configurations.
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