Abstract
The molecular and crystal structure is reported for the major diastereoisomer formed in a sterically hindered reaction of a substituted dinaphthodithiepine. The structure lends support to a reaction mechanism and transition state postulated to explain the experimentally determined preferential formation of this diastereoisomer over the minor component.
The racemic title compound, C
34
H
32
OS
2
, comprises an atropisomeric binaphthyl dithioacetal substituted at the methylene carbon atom with a chiral benzyl alcohol. The two naphthalene ring systems are additionally substituted at the 3,3′-position with isopropyl groups. The overall stereochemistry is defined as
aS,R
and
aR,S
. The hydroxyl group forms an intramolecular O—H⋯S hydrogen bond to one of the sulfur atoms. The crystal structure contains weak C—H⋯π interactions that link the molecules into extended arrays.