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Chirally Modified n ‐Butyllithium: Tuning the Composition, Structure, and Enantioselectivity with Modular Fencholates
Author(s) -
Goldfuss Bernd,
Steigelmann Melanie,
Rominger Frank
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001117)39:22<4133::aid-anie4133>3.0.co;2-x
Subject(s) - benzaldehyde , aggregate (composite) , substituent , lithium (medication) , modular design , butyllithium , composition (language) , chemistry , medicinal chemistry , materials science , organic chemistry , computer science , nanotechnology , catalysis , psychology , art , operating system , literature , psychiatry
2:2 instead of 3:1 is the ratio between the lithium anisylfencholate 1 and the n BuLi units in the aggregate formed from these components (see structure) when the substituent is changed from X=H to X=SiMe 3 . DFT calculations confirm the different stability sequences of the 2:2 and 3:1 aggregates with the two different X substituents. The 2:2 aggregate gives a higher enantioselectivity (80 % ee ) than the 3:1 aggregate in the n BuLi addition to benzaldehyde.