A pentenyl dianion-based strategy for convergent synthesis of ene-1,5-diols

被引：56

作者：

Bahadoor, AB ^{[1
]}

Flyer, A ^{[1
]}

Micalizio, GC ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, Sterling Chem Lab, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2005年 / 127卷 / 11期

关键词：

D O I：

10.1021/ja050039+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent two-step process is described for the synthesis of ene-1,5-diols that provides for union of two carbonyl electrophiles via a formal pentenyl dianion equivalent. Copyright © 2005 American Chemical Society.

引用

页码：3694 / 3695

页数：2

共 25 条

[1]

Bode JW, 2001, ANGEW CHEM INT EDIT, V40, P2082, DOI 10.1002/1521-3773(20010601)40:11<2082::AID-ANIE2082>3.0.CO

[2]

2-1

[3] GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058

[4] ACCURATE DETERMINATION OF THE EXTENT TO WHICH THE S(E)2' REACTIONS OF AN ALLENYLSILANE ARE STEREOSPECIFICALLY ANTI [J].

BUCKLE, MJC ;

FLEMING, I .

TETRAHEDRON LETTERS, 1993, 34 (14) :2383-2386

[5] SCOPE AND STEREOCHEMICAL COURSE OF THE ADDITION OF (TRIMETHYLSILYL)ALLENES TO KETONES AND ALDEHYDES - A REGIOCONTROLLED SYNTHESIS OF HOMOPROPARGYLIC ALCOHOLS [J].

DANHEISER, RL ;

CARINI, DJ ;

KWASIGROCH, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) :3870-3878

[6] Titanium-mediated formation of 1,2-disubstituted cyclopropanols from esters and alkenes. A new approach to the synthesis of 3,11-dimethylnonacosan-2-one, a sex pheromone of the German cockroach [J].

Epstein, OL ;

Kulinkovich, OG .

TETRAHEDRON LETTERS, 1998, 39 (13) :1823-1826

[7] DOUBLE STEREODIFFERENTIATING ALDOL REACTIONS - THE DOCUMENTATION OF PARTIALLY MATCHED ALDOL BOND CONSTRUCTIONS IN THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS [J].

EVANS, DA ;

DART, MJ ;

DUFFY, JL ;

RIEGER, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :9073-9074

[8] Enantioselective synthesis of 1,5-anti- and 1,5-syn-diols using a highly diastereoselective one-pot double allylboration reaction sequence [J].

Flamme, EM ;

Roush, WR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13644-13645

[9] SYNTHESIS OF THE C(3)-C(15) SEGMENT OF RUTAMYCIN-B VIA A C(8)-C(9) FRAGMENT ASSEMBLY ALDOL REACTION - METAL DEPENDENCE OF THE ALDEHYDE AND ENOLATE DIASTEREOFACIAL SELECTIVITIES [J].

GUSTIN, DJ ;

VANNIEUWENHZE, MS ;

ROUSH, WR .

TETRAHEDRON LETTERS, 1995, 36 (20) :3447-3450

[10] GENERATION AND REACTIONS OF LOW-VALENT TITANIUM ALKOXIDE-ACETYLENE COMPLEXES - A PRACTICAL PREPARATION OF ALLYL ALCOHOLS [J].

HARADA, K ;

URABE, H ;

SATO, F .

TETRAHEDRON LETTERS, 1995, 36 (18) :3203-3206

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