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Stereoselective synthesis of alcohols, XLI. Chirality transfer to generate quaternary stereogenic centers by an allylboration reaction
Author(s) -
Hoffmann Reinhard W.,
Schlapbach Achim
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101205
Subject(s) - stereocenter , chemistry , chirality (physics) , stereoselectivity , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
The acyclic alcohols 13 and 14 having a neighboring quaternary stereogenic center can be obtained in diastereoselectivities of > 95% by addition of the ß,γ,γ‐trisubstituted allylboronates 12 to aldehydes. Starting from the nonracemic allylboronates 19 of presumed 84–92% e.e., we have obtained the alcohols 13a and 14a with the corresponding levels of the e.e.