Abstract
Reaction of N-sulfonyl amino acid with 1 equiv. of BH3 THF easily gave the oxazaborolidinone which promoted the aldol reaction of a variety of aldehydes with silyl ketene acetals with very high enantioselectivity. For example, isobutyrate aldols were obtained with >96% ee and acetate aldols were obtained with >98% ee by using a silyl nucleophile derived from ethyl 1, 3-dithiolane-2-carboxylate. The level of the selectivity is surely acceptable for practical syntheses although the promoter is used as stoichiometric amounts. The scope and limitation of the oxazaborolidinone-promoted aldol reaction will be discussed by surveying the stereochemical outcome of the reaction inducing the high enantioselectivity.
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.
