Sequential Pd-Catalyzed Asymmetric Allene Diboration/α-Aminoallylation
- 7 December 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (1) , 74-75
- https://doi.org/10.1021/ja057020r
Abstract
Pd-catalyzed enantioselective diboration of prochiral allenes provides adducts which participate in highly selective allylation reactions with primary imines. The allylation product is a vinyl boronate which may be oxidized to give nonracemic Mannich products (87−97% ee). Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.Keywords
This publication has 20 references indexed in Scilit:
- Stereospecific, Enantioselective Allylation of α‐Hydrazono Esters by Using Allyltrichlorosilanes with BINAP Dioxides as Neutral‐Coordinate OrganocatalystsAngewandte Chemie International Edition in English, 2004
- Palladium-Catalyzed Enantioselective Diboration of Prochiral AllenesJournal of the American Chemical Society, 2004
- α-Aminoallylation of Aldehydes with Ammonia: Stereoselective Synthesis of Homoallylic Primary AminesJournal of the American Chemical Society, 2004
- The First Catalytic Asymmetric Allylation of Imines with the Tetraallylsilane−TBAF−MeOH System, Using the Chiral Bis-π-allylpalladium ComplexThe Journal of Organic Chemistry, 2004
- Rhodium-Catalyzed Enantioselective Diboration of Simple AlkenesJournal of the American Chemical Society, 2003
- An Efficient Synthesis of N-Unsubstituted Imines as Organoborane Adducts Stable at Room Temperature: New Promising Intermediates for SynthesisJournal of the American Chemical Society, 2000
- Catalytic, Enantioselective Alkylations of N,O-AcetalsThe Journal of Organic Chemistry, 1999
- Catalytic Asymmetric Allylation of Imines via Chiral Bis-π-allylpalladium ComplexesJournal of the American Chemical Society, 1998
- Enantioselective Synthesis of Homoallylamines by Nucleophilic Addition of Chirally Modified Allylboron Reagents to IminesAngewandte Chemie International Edition in English, 1997
- Hydroboration. XI. The Hydroboration of Acetylenes—A Convenient Conversion of Internal Acetylenes into cis-Olefins and of Terminal Acetylenes into AldehydesJournal of the American Chemical Society, 1961