Unknown

Dataset Information

0

Synthesis of cyclic chiral ?-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.


ABSTRACT: A copper(i)-catalyzed dearomative borylation of N-alkoxycarbonyl protected indole-3-carboxylates has been developed. The boron addition in this reaction occurred regioselectively at the 2-position of indoles followed by diastereoselective protonation, affording the corresponding stable cyclic chiral ?-amino boronates (2-borylindolines) in moderate to good yields with excellent diastereo- and enantioselectivities. The product 2c could be used as a versatile precursor to undergo subsequent stereoselective transformations, delivering highly functionalized 2,3,3-trisubstituted chiral indolines.

SUBMITTER: Chen L 

PROVIDER: S-EPMC6050576 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature

altmetric image

Publications

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.

Chen Lili L   Shen Jun-Jian JJ   Gao Qian Q   Xu Senmiao S  

Chemical science 20180612 26


A copper(i)-catalyzed dearomative borylation of <i>N</i>-alkoxycarbonyl protected indole-3-carboxylates has been developed. The boron addition in this reaction occurred regioselectively at the 2-position of indoles followed by diastereoselective protonation, affording the corresponding stable cyclic chiral α-amino boronates (2-borylindolines) in moderate to good yields with excellent diastereo- and enantioselectivities. The product <b>2c</b> could be used as a versatile precursor to undergo subs  ...[more]

Similar Datasets

| S-EPMC10057014 | biostudies-literature
| S-EPMC6260458 | biostudies-literature
| S-EPMC6664198 | biostudies-literature
| S-EPMC5639465 | biostudies-literature
| S-EPMC6956864 | biostudies-literature
| S-EPMC2825324 | biostudies-literature
| S-EPMC5087316 | biostudies-literature
| S-EPMC4809423 | biostudies-literature
| S-EPMC4770434 | biostudies-other
| S-EPMC4562282 | biostudies-literature