Asymmetric Synthesis, Characterization and Stereoselectivity of Novel 1-{2-[(1R,2S)-2-(Chloromethyl)cyclopropyl]ethyl}-4-methoxybenzene via Boronate Complex

被引：0

作者：

Hussain, Habib ^{[1
]}

Gilani, Syeda Rubina ^{[1
]}

Ali, Zulfiqar ^{[1
]}

Hussain, Imdad ^{[1
]}

机构：

[1] Univ Engn & Technol, Dept Chem, Lahore, Pakistan

来源：

ASIAN JOURNAL OF CHEMISTRY | 2014年 / 26卷 / 08期

关键词：

Boronic ester; Boronate complex; Aryllithium; Electrophiles; Cyclopropanation; Stereoselectivity; ATE COMPLEXES; ESTERS;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel 1-[2-{(1R,2S)-2-(chloromethyl)cyclopropyl]ethyl}-4-methoxybenzene was synthesized by cyclopropanation reaction through a novel route. Carbamate was reacted with 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane to form boronic ester which was further treated with 1-bromo-3,5-bis(trifluoromethyl) benzene in the presence of n-BuLi and nucleophilic boronate complex was synthesized. 1-[2{(1R, 2S)-2-(chloromethyl) cyclopropyl] ethyl}-4-methoxybenzene was then prepared by reacting boronate complex with different electrophiles like trichloroisocyanuric acid (TCCA) and N-chlorosuccinimide (NCS). Yields and diastereomeric ratios (d.r) were studied by using various aryl lithiums and electrophiles at different temperatures. Best yield, diastereomeric ratio (d.r), enantiomeric ratio (e.r), enantiomeric excess (e.e), enantiospecificity and [alpha](D) were 67 %, 2.1:1, 68.6: 28.9, 39.7, 0.41 and +3.84, respectively.

引用

页码：2437 / 2442

页数：6

共 11 条

[1] CHIRAL SYNTHESIS VIA ORGANOBORANES .16. BOROXAZOLIDONES DERIVED FROM ALPHA-AMINO-ACIDS AND BORINIC OR BORONIC ESTERS - A SIMPLE PROCEDURE FOR UPGRADING BORINATES AND BORONATES TO MATERIALS OF HIGH OPTICAL PURITY
BROWN, HC
GUPTA, AK
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) : 73 - 81
[2] Anodic preparation of [Re2Cp2(CO)6]2+:: A dimeric dication that provides the powerful one-electron oxidant [ReCp(CO)3]+
Chong, DS
Nafady, A
Costa, PJ
Calhorda, MJ
Geiger, WE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) : 15676 - 15677
[3] Catalytic enantioselective transformations of borylated substrates: Preparation and synthetic applications of chiral alkylboronates
Hall, Dennis G.
Lee, Jack C. H.
Ding, Jinyue
[J]. PURE AND APPLIED CHEMISTRY, 2012, 84 (11) : 2263 - 2277
[4] Enantioselective Preparation of a Stable Boronate Complex Stereogenic Only at Boron
Kaiser, Peter F.
White, Jonathan M.
Hutton, Craig A.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (49) : 16450 - +
[5] Ate Complexes of Secondary Boronic Esters as Chiral Organometallic-Type Nucleophiles for Asymmetric Synthesis
Larouche-Gauthier, Robin
Elford, Tim G.
Aggarwal, Varinder K.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (42) : 16794 - 16797
[6] Chiral Boronate Derivatives via Catalytic Enantioselective Conjugate Addition of Grignard Reagents on 3-Boronyl Unsaturated Esters and Thioesters
Lee, Jack Chang Hung
Hall, Dennis G.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (16) : 5544 - +
[7] α-Hydroxyalkyl Heterocycles via Chiral Allylic Boronates: Pd-Catalyzed Borylation Leading to a Formal Enantioselective lsomerization of Allylic Ether and Amine
Lessard, Stephanie
Peng, Feng
Hall, Dennis G.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (28) : 9612 - 9613
[8] Asymmetric allylboration of ketones catalyzed by chiral diols
Lou, Sha
Moquist, Philip N.
Schaus, Scott E.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12660 - 12661
[9] Asymmetric conjugate addition of alkynylboronates to enones: Rationale for the intriguing catalysis exerted by binaphthols
Pellegrinet, SC
Goodman, JM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (10) : 3116 - 3117
[10] STRUCTURE OF INTRAMOLECULAR BORON-AMINE COMPLEXES AND PROPOSAL OF TETRAHEDRAL CHARACTER FOR CORRELATION BETWEEN MOLECULAR-STRUCTURE AND BARRIER TO DISSOCIATION OF THE N-B BONDS
TOYOTA, S
OKI, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (07) : 1832 - 1840

← 1 2 →