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本文引用的文献

1
Identification of an activated catalyst in the iridium-catalyzed allylic amination and etherification. Increased rates, scope, and selectivity.铱催化烯丙基胺化和醚化反应中活性催化剂的鉴定。反应速率、范围和选择性的提高。
J Am Chem Soc. 2003 Nov 26;125(47):14272-3. doi: 10.1021/ja038319h.
2
Asymmetric, catalytic synthesis of alpha-chiral amines using a novel bis(phosphine) monoxide chiral ligand.使用新型单氧化双（膦）手性配体不对称催化合成α-手性胺。
J Am Chem Soc. 2003 Nov 26;125(47):14260-1. doi: 10.1021/ja038291+.
3
Molybdenum and tungsten imido alkylidene complexes as efficient olefin-metathesis catalysts.钼和钨亚胺基亚烷基配合物作为高效的烯烃复分解催化剂。
Angew Chem Int Ed Engl. 2003 Oct 6;42(38):4592-633. doi: 10.1002/anie.200300576.
4
Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines. A practical synthesis of alpha-chiral amines.二烷基锌对N-二苯基膦酰亚胺的催化对映选择性加成反应。α-手性胺的实用合成方法。
J Am Chem Soc. 2003 Feb 19;125(7):1692-3. doi: 10.1021/ja027673x.
5
Regio- and enantioselective allylic amination of achiral allylic esters catalyzed by an iridium-phosphoramidite complex.铱-亚磷酰胺配合物催化的非手性烯丙基酯的区域和对映选择性烯丙基胺化反应。
J Am Chem Soc. 2002 Dec 25;124(51):15164-5. doi: 10.1021/ja028614m.
6
N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines.N-叔丁基亚磺酰亚胺：用于胺类不对称合成的通用中间体。
Acc Chem Res. 2002 Nov;35(11):984-95. doi: 10.1021/ar020066u.
7
Asymmetric, catalytic phenyl transfer to imines: highly enantioselective synthesis of diarylmethylamines.不对称催化苯基转移至亚胺：二芳基甲胺的高对映选择性合成
Angew Chem Int Ed Engl. 2002 Oct 4;41(19):3692-4; 3522. doi: 10.1002/1521-3773(20021004)41:19<3692::AID-ANIE3692>3.0.CO;2-N.
8
The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands.基于[2.2]对环芳烷的N,O-配体催化的亚胺的不对称二烷基锌加成反应。
J Am Chem Soc. 2002 May 29;124(21):5940-1. doi: 10.1021/ja025831e.
9
Allylic Amination.烯丙基胺化反应
Chem Rev. 1998 Jun 18;98(4):1689-1708. doi: 10.1021/cr970343o.
10
Pd asymmetric allylic alkylation (AAA). A powerful synthetic tool.钯催化不对称烯丙基烷基化反应（AAA）：一种强大的合成工具。
Chem Pharm Bull (Tokyo). 2002 Jan;50(1):1-14. doi: 10.1248/cpb.50.1.

用于对映选择性烯丙基胺化的铱催化剂中立体化学元素的编辑。

Editing the stereochemical elements in an iridium catalyst for enantioselective allylic amination.

作者信息

Leitner Andreas, Shu Chutian, Hartwig John F

机构信息

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107, USA.

出版信息

Proc Natl Acad Sci U S A. 2004 Apr 20;101(16):5830-3. doi: 10.1073/pnas.0307967101. Epub 2004 Apr 5.

DOI:10.1073/pnas.0307967101
PMID:15067140
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC395994/
Abstract

Individual diastereomeric phosphoramidites and mixtures of diastereomeric phosphoramidites were evaluated in the iridium-catalyzed amination of allylic carbonates. The original process was conducted with a phosphoramidite ligand containing a resolved 2,2-dihydroxy-1,1-binaphthyl (BINOL) group and a diastereomerically and enantiomerically pure bis(phenethyl)amino group. Evaluation of the structure of the active catalyst and relative rates for reactions in the presence of catalysts containing diastereomeric ligands led to the identification of a phosphoramidite that provided the amination product with enantiomeric excess similar to the original, more structurally and stereochemically complex ligand and that contains a racemic BINOLate and an N-benzylphenethylamino group on phosphorus.

摘要

在铱催化的烯丙基碳酸酯胺化反应中，对各个非对映异构亚磷酰胺及非对映异构亚磷酰胺混合物进行了评估。最初的反应过程使用了一种亚磷酰胺配体，该配体含有拆分的2,2 - 二羟基 - 1,1 - 联萘基（联萘酚，BINOL）基团以及非对映异构和对映异构纯的双（苯乙基）氨基。对活性催化剂的结构以及在含有非对映异构配体的催化剂存在下反应的相对速率进行评估后，确定了一种亚磷酰胺，该亚磷酰胺提供的胺化产物的对映体过量与原始的、结构和立体化学更复杂的配体相似，并且在磷上含有外消旋联萘酚盐和N - 苄基苯乙氨基。