Determination of the absolute configuration of 1-arylethane-1,2-diols by a nonempirical analysis of the CD spectra of their 4-biphenylboronates

被引：31

作者：

Superchi, S ^{[1
]}

Donnoli, MI ^{[1
]}

Rosini, C ^{[1
]}

机构：

[1] Univ Basilicata, Dipartimento Chim, I-85100 Potenza, Italy

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 13期

关键词：

D O I：

10.1021/ol991146+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 1-Arylethane-1,2-diols 1, reacting with 4-biphenylboronic acid 2, form the conformationally defined boronates 3 where the aryl and biphenyl chromophores assume a fixed and known relative disposition. These chromophores thus define an exciton coupled system, whose chirality (revealed by the sign of the biphenyl On band at 260 nm) allows an unambiguous assignment of the absolute configuration of the stereogenic center. This approach provides the hitherto unreported absolute configuration of diols 1c-f.

引用

页码：2093 / 2096

页数：4

共 44 条

[1] NEW LIGANDS AND IMPROVED ENANTIOSELECTIVITIES FOR THE ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

BECKER, H ;

KING, SB ;

TANIGUCHI, M ;

VANHESSCHE, KPM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :3940-3941

[2] Total synthesis of (+)-duocarmycin A, epi-(+)-duocarmycin A and their unnatural enantiomers: Assessment of chemical and biological properties [J].

Boger, DL ;

McKie, JA ;

Nishi, T ;

Ogiku, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (02) :311-325

[3] CIRCULAR DICHROISM STUDIES ON CUPRAMMONIUM COMPLEXES OF DIOLS AND AMINO-ALCOHOLS [J].

BUKHARI, STK ;

GUTHRIE, RD ;

SCOTT, AI ;

WRIXON, AD .

TETRAHEDRON, 1970, 26 (15) :3653-&

[4] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[5] ABSOLUTE CONFIGURATIONAL STUDIES OF VICINAL GLYCOLS AND AMINO ALCOHOLS .2. WITH PR(DPM)3 [J].

DILLON, J ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5417-5422

[6] ABSOLUTE CONFIGURATIONAL STUDIES OF VICINAL GLYCOLS AND AMINO ALCOHOLS .1. WITH NI(ACAC)2 [J].

DILLON, J ;

NAKANISHI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (19) :5409-5417

[7] A NEW SYNTHESIS OF ARYL FLUORIDES - THE REACTION OF CESIUM FLUOROXYSULFATE WITH ARYLBORONIC ACIDS AND DERIVATIVES [J].

DIORAZIO, LJ ;

WIDDOWSON, DA ;

CLOUGH, JM .

TETRAHEDRON, 1992, 48 (37) :8073-8088

[8] BAKERS YEAST-MEDIATED PREPARATION OF OPTICALLY-ACTIVE ARYL ALCOHOLS AND DIOLS FOR THE SYNTHESIS OF CHIRAL HYDROXY-ACIDS [J].

FERRABOSCHI, P ;

GRISENTI, P ;

MANZOCCHI, A ;

SANTANIELLO, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2469-2474

[9] OPTICALLY-ACTIVE AMINES .33. CIRCULAR-DICHROISM OF SUBSTITUTED PHENYLCARBINOLS [J].

FONTANA, LP ;

SMITH, HE .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3386-3389

[10]

Frelek J, 1997, CHIRALITY, V9, P578, DOI 10.1002/(SICI)1520-636X(1997)9:5/6<578::AID-CHIR27>3.3.CO

← 1 2 3 4 5 →