Abstract
As part of a program aimed at exploring the utility of remote asymmetric centres to control the addition of nucleophiles to carbonyl functions, it was discovered that homochiral ester derivatives of β-boronate carbonyl compounds do not control the addition of alkyllithium, Grignard or cuprate-based nucleophiles. However, use of a lithium ester enolate nucleophile exhibits medium to high remote diastereocontrol in aldol additions to carbonyl functions.
Highlights
The application of remote chiral centres for controlling asymmetric transformations is difficult,[1] though beginning to attract greater attention due to the range over which diastereocontrol may be effected.[2]
Our initial studies in this area involved the development of an achiral intramolecular boronate function to control the relative stereochemistry of aldol reactions.[3]
Parallel studies were conducted by Molander et al on 1,7-asymmetric induction[4] and by ourselves on 1,6-asymmetric induction[5] involving the use of a homochiral boronate unit for controlling remote asymmetric reduction of an intramolecular carbonyl function.[6]
Summary
The application of remote chiral centres for controlling asymmetric transformations is difficult,[1] though beginning to attract greater attention due to the range over which diastereocontrol may be effected.[2].
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
