In many biological materials with a hierarchical structure there is an intriguing and unique mechanism responsible for the 'propagation' of order from the molecular to the nano-or micro-scale level. Here we present a much simpler molecular system built of achiral mesogenic dimeric molecules that shows a similar complexity with four levels of structural chirality (i) layer chirality, (ii) helicity of a basic 4-layer repeating unit, (iii) a helix with a pitch of several layers and (iv) mesoscopic helical filaments. As seen in many biological systems, there is a coupling between chirality at different levels. The structures were identified by a combination of hard and soft x-ray diffraction measurements, optical studies and theoretical modelling.One Sentence Summary: Simple molecular system exhibits complex hierarchical structure with chirality coupling between different structural levels.

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In contrast to the corresponding enolate, the metalloenamine obtained from (IV) + (II) undergoes α‐alkylation in a regio‐ and stereoselective fashion even with less reactive electrophiles such as (III) and (V), thus giving access to the desired trans‐α‐alkyl‐β‐silyl ketones (six examples given).

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