Enantio- and Diastereoselective Tandem Zn-Promoted Brook Rearrangement/Ene-Allene Carbocyclization Reaction

被引：46

作者：

Unger, Rozalia ^{[1
,2
]}

Weisser, Fritz ^{[1
,2
]}

Chinkov, Nicka ^{[1
,2
]}

Stanger, Amnon ^{[1
,2
]}

Cohen, Theodore ^{[3
]}

Marek, Ilan ^{[1
,2
]}

机构：

[1] Technion Israel Inst Technol, Mallat Family Lab Organ Chem, Schulich Fac Chem, IL-32000 Haifa, Israel

[2] Technion Israel Inst Technol, Lise Meitner Minerva Ctr Computat Quantum Chem, IL-32000 Haifa, Israel

[3] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 08期

关键词：

CATALYTIC ASYMMETRIC VINYLATION; CARBONYL ALLYLATION REACTIONS; CHIRAL QUATERNARY CENTERS; ZINCA-ENE-ALLENE; CONFIGURATIONAL STABILITY; STEREOSELECTIVE-SYNTHESIS; CINNAMYL DERIVATIVES; TERTIARY ALCOHOLS; AB-INITIO; KETONES;

D O I：

10.1021/ol9004036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The zinc-catalyzed addition of various alkynes to acylsilanes followed by a Zn-Brook rearrangement and either the Zn-ene-allene or Zn-yne-allene cyclization led to the enantio- and diastereoselective formation of carbocycles in a single-pot operation.

引用

页码：1853 / 1856

页数：4

共 64 条

[1] AB-INITIO THEORETICAL INVESTIGATION ON THE WRIGHT-WEST AND WITTIG ANIONIC MIGRATION REACTIONS [J].

ANTONIOTTI, P ;

TONACHINI, G .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) :3622-3632

[2] STEREOCHEMISTRY OF SILYLCARBINOL TO SILYL ETHER REARRANGEMENT [J].

BIERNBAUM, MS ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (23) :6221-+

[3] STEREOCHEMISTRY AT ASYMMETRIC CARBON IN SILYLCARBINOL TO ALKOXYSILANE REARRANGEMENT [J].

BROOK, AG ;

PASCOE, JD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (23) :6224-&

[4] Enantioselective alkynylation of ketones catalyzed by Zn(salen) complexes [J].

Cozzi, PG .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (25) :2895-2898

[5] Development of bifunctional salen catalysts:: Rapid, chemoselective alkylations of α-ketoesters [J].

DiMauro, EF ;

Kozlowski, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12668-12669

[6] Catalytic asymmetric addition of ZnPh2 to ketones:: Enantioselective formation of quaternary stereocenters [J].

Dosa, PI ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) :445-446

[7] A practical catalytic asymmetric addition of alkyl groups to ketones [J].

García, C ;

LaRochelle, LK ;

Walsh, PJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (37) :10970-10971

[8] Stereoselective heteroatom-assisted allylic alkylation of cyclic ethers with Grignard reagents. A convenient route to enantiomerically pure carbocycles [J].

Heron, NM ;

Adams, JA ;

Hoveyda, AH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (26) :6205-6206

[9] RETRO [1,4]-BROOK REARRANGEMENTS OF NONCONJUGATED SECONDARY ALPHA-LITHIO ETHERS - PROOF OF STEREOSPECIFICITY AND OF RETENTION OF CONFIGURATION AT THE CARBANION CENTER [J].

HOFFMANN, R ;

BRUCKNER, R .

CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (12) :2731-2739

[10] Synthetic applications of carbolithiation transformations [J].

Hogan, Anne-Marie L. ;

O'Shea, Donal F. .

CHEMICAL COMMUNICATIONS, 2008, (33) :3839-3851

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