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Conformational Analysis of oligo ‐1,3‐Dioxanylmethanes
Author(s) -
Trieselmann Thomas,
Hoffmann Reinhard W.,
Menzel Karsten
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1292::aid-ejoc1292>3.0.co;2-6
Subject(s) - chemistry , ring (chemistry) , substrate (aquarium) , stereoselectivity , stereochemistry , preference , organic chemistry , catalysis , oceanography , economics , microeconomics , geology
Stereoselective synthesis of a series of 1,3‐dioxan‐4‐ylmethanes 1 − 9 has been achieved by use of solely substrate‐based asymmetric induction. The simple C 2 ‐symmetric bis(dioxanyl)methane 1 has a greater than 99% conformational preference at the two inter‐ring bonds for the conformation 1a . The homologous structures 3−9 contain up to five dioxanylmethane units, maintaining a high conformational preference in each of the bis(dioxanyl)methane units. Thus, these flexible compounds reach a conformational preference in excess of 90% over up to eight rotatable inter‐ring bonds. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)