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Boron/Zinc Exchange Reaction in the Diastereoselective Arylation of N ‐Protected L ‐Prolinal
Author(s) -
Martins Bruna S.,
Lüdtke Diogo S.
Publication year - 2014
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/ejoc.201402508
Subject(s) - chemistry , diastereomer , stereocenter , diethylzinc , aryl , substituent , vicinal , zinc , chirality (physics) , boron , medicinal chemistry , chelation , stereochemistry , asymmetric induction , organic chemistry , enantioselective synthesis , alkyl , catalysis , nambu–jona lasinio model , chiral symmetry breaking , quark , physics , quantum mechanics
The diastereoselective arylation of chiral, non‐racemic, N ‐trityl‐protected L ‐prolinal has been investigated. The reactive aryl groups were generated by a boron/zinc exchange reaction between arylboronic acids and diethylzinc. The reactions proceeded in a highly diastereoselective fashion, and the resulting amino alcohols possessing two vicinal stereocenters were obtained in diastereomeric ratios of >20:1, regardless of the substituent at the transferable aryl group. The diastereoselectivity of the reactions is believed to be the result of an energetically favored Felkin–Anh transition state, with the competing Cram‐chelation pathway precluded due to the presence of the bulky N ‐trityl protecting group.