Aminative Umpolung of Aldehydes to α-Amino Anion Equivalents for Pd-Catalyzed Allylation: An Efficient Synthesis of Homoallylic Amines

被引：30

作者：

Ding, Lei

Chen, Jing

Hu, Yifan

Xu, Juan

Gong, Xing

Xu, Dongfang

Zhao, Baoguo ^{[1
]}

Li, Hexing

机构：

[1] Shanghai Normal Univ, Key Lab Resource Chem, Educ Minist, Shanghai 200234, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 03期

关键词：

DECARBOXYLATIVE ALLYLIC ALKYLATIONS; DIPHENYLGLYCINATE IMINES; CARBONYL-COMPOUNDS; COUPLING REACTIONS; DERIVATIVES; GENERATION; KETONES; ESTERS; NUCLEOPHILES; CHEMISTRY;

D O I：

10.1021/ol4034012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An attractive strategy for generation of alpha-amino anions from aldehydes with applications in synthesis of homoallylic amines is described. Aromatic aldehydes can be converted to alpha-amino anion equivalents via amination with 2,2-diphenylglycine and Subsequent decarboxylation. The in situ generated alpha-imino anions are highly reactive for Pd-catalyzed allylation, forming the corresponding homoallylic amines in high yields with excellent regioselectivity.

引用

收藏

页码：720 / 723

页数：4

相关论文

共 39 条

[1] Regioselective, diastereoselective, and enantioselective lithiation-substitution sequences: Reaction pathways and synthetic applications [J].

Beak, P ;

Basu, A ;

Gallagher, DJ ;

Park, YS ;

Thayumanavan, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (11) :552-560

[2] The enantioselective Tsuji allylation [J].

Behenna, DC ;

Stoltz, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15044-15045

[3]

Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/nchem.1222, 10.1038/NCHEM.1222]

[4] Aldehyde N,N-dialkylhydrazones as neutral acyl anion equivalents:: Umpolung of the imine reactivity [J].

Brehme, Rainer ;

Enders, Dieter ;

Fernandez, Rosario ;

Lassaletta, Jose M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (34) :5629-5660

[5] Organocatalytic umpolung: N-heterocyclic carbenes and beyond [J].

Bugaut, Xavier ;

Glorius, Frank .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3511-3522

[6] Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives [J].

Burger, Erin C. ;

Tunge, Jon A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10002-10003

[7] 40 YEARS OF UMPOLUNG IN ORGANOMETALLIC CHEMISTRY - FROM CARBANIONIC NUCLEOPHILES TO METALLIC ELECTROPHILES [J].

EISCH, JJ .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 500 (1-2) :101-115

[8] One-Pot Tandem Decarboxylative Allylation-Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes [J].

Fields, Wendy H. ;

Khan, Ali K. ;

Sabat, Michal ;

Chruma, Jason J. .

ORGANIC LETTERS, 2008, 10 (22) :5131-5134

[9] Palladium-Catalyzed Decarboxylative Benzylation of Diphenylglycinate Imines [J].

Fields, Wendy H. ;

Chruma, Jason J. .

ORGANIC LETTERS, 2010, 12 (02) :316-319

[10] Ir-catalyzed regio- and enantioselective decarboxylative allylic Alkylations [J].

He, Hu ;

Zheng, Xiao-Jian ;

Li, Yi ;

Dai, Li-Xin ;

You, Shu-Li .

ORGANIC LETTERS, 2007, 9 (21) :4339-4341

← 1 2 3 4 →