Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

Yang Zang; Iwao Ojima

doi:10.1016/j.tetlet.2015.01.047

Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

Yang Zang
, Iwao Ojima

Chemistry

Stony Brook University

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and enantiopurity (93-95% ee). These amides were applied to the synthesis of fused polycyclic alkaloids in a short sequence of steps.

Original language	English
Article number	45717
Pages (from-to)	3288-3292
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2015.01.047
State	Published - May 25 2015

Keywords

Alkaloids
Asymmetric allylic amination
BOP ligands
Palladium catalysts

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10.1016/j.tetlet.2015.01.047

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title = "Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids",

abstract = "Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and enantiopurity (93-95\% ee). These amides were applied to the synthesis of fused polycyclic alkaloids in a short sequence of steps.",

keywords = "Alkaloids, Asymmetric allylic amination, BOP ligands, Palladium catalysts",

author = "Yang Zang and Iwao Ojima",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

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doi = "10.1016/j.tetlet.2015.01.047",

language = "English",

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T1 - Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

AU - Zang, Yang

AU - Ojima, Iwao

PY - 2015/5/25

Y1 - 2015/5/25

N2 - Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and enantiopurity (93-95% ee). These amides were applied to the synthesis of fused polycyclic alkaloids in a short sequence of steps.

AB - Abstract Pd-catalyzed asymmetric allylic amination reaction of piperonylamides and a 2-siloxymethylcyclohexenyl carbonate, using chiral biphenol-based diphosphinite (BOP) ligands gave the corresponding cyclohexenylpiperonylamides in excellent yield and enantiopurity (93-95% ee). These amides were applied to the synthesis of fused polycyclic alkaloids in a short sequence of steps.

KW - Alkaloids

KW - Asymmetric allylic amination

KW - BOP ligands

KW - Palladium catalysts

UR - https://www.scopus.com/pages/publications/84929578845

U2 - 10.1016/j.tetlet.2015.01.047

DO - 10.1016/j.tetlet.2015.01.047

M3 - Article

AN - SCOPUS:84929578845

SN - 0040-4039

VL - 56

SP - 3288

EP - 3292

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

M1 - 45717

ER -

Pd-catalyzed asymmetric allylic amination with BOP ligands and its applications to the synthesis of fused polycyclic alkaloids

Abstract

Keywords

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