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Boston College

1. Hong, Kai. Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters.

Degree: PhD, Chemistry, 2015, Boston College

Platinum-catalyzed enantioselective 1,4-diboration of cyclic 1,3-dienes is reported, providing enantioenriched 1,4-bis(boronic) esters in good yield and up to 96:4 er. The analogous diboration reaction of imines generated enantioenriched alpha-amino boronic esters, which are valuable therapeutic candidates and useful synthetic building blocks. Alpha-substituted allyl bis(boronic) esters, which are derived from 1,2-diboration of 1,3-dienes, undergo double allylation with 1,4-dicarbonyls to afford cyclic 1,4-diols bearing four contiguous stereocenters in a one-pot fashion with moderate to excellent diastereoselectivity. The development of a synthesis of geminal bis(boronic) esters is disclosed. These unique compounds were utilized in an alkoxide-promoted deborylative alkylation to access primary, secondary and tertiary boronic esters. Advisors/Committee Members: James P. Morken (Thesis advisor).

Subjects/Keywords: Alkylation; Allylboration; Diboration; Diene; Imine; Pt-catalyzed

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Hong, K. (2015). Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters. (Doctoral Dissertation). Boston College. Retrieved from http://dlib.bc.edu/islandora/object/bc-ir:104130

Chicago Manual of Style (16th Edition):

Hong, Kai. “Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters.” 2015. Doctoral Dissertation, Boston College. Accessed January 19, 2020. http://dlib.bc.edu/islandora/object/bc-ir:104130.

MLA Handbook (7th Edition):

Hong, Kai. “Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters.” 2015. Web. 19 Jan 2020.

Vancouver:

Hong K. Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters. [Internet] [Doctoral dissertation]. Boston College; 2015. [cited 2020 Jan 19]. Available from: http://dlib.bc.edu/islandora/object/bc-ir:104130.

Council of Science Editors:

Hong K. Platinum-Catalyzed Enantioselective Diboration of 1,3-Dienes and Imines and Functionalization of 1,2- and Geminal Bis(boronic) Esters. [Doctoral Dissertation]. Boston College; 2015. Available from: http://dlib.bc.edu/islandora/object/bc-ir:104130

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