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Herein we report a highly efficient and enantiospecific borylation method to synthesize a wide range of enantiopure (>99 % ee) α‐amino tertiary boronic esters. The configurationally stable α‐N‐Boc substituted tertiary organolithium species and pinacolborane (HBpin) underwent enantiospecific borylation at −78 °C with the formation of a new stereogenic C−B bond. This reaction has a broad scope, enabling the synthesis of various α‐amino tertiary boronic esters in excellent yields and, importantly, with universally excellent enantiospecificity (>99 % es) and complete retention of configuration. Enantiospecific borylation: A highly enantiospecific borylation of configurationally stable α‐N‐Boc substituted tertiary organolithium species and HBpin has been developed to synthesize various α‐amino tertiary boronic esters through the formation of a new C−B bond with excellet enantiopurity and complete retention of configuration. [ABSTRACT FROM AUTHOR]