A head-to-head comparison of α- and β-alkoxy effects on stereoselectivity.: Nucleophilic additions to a cyclohexanone substituted with five axial C-O bonds

被引：5

作者：

Paquette, LA ^{[1
]}

Tae, JS ^{[1
]}

机构：

[1] Ohio State Univ, Evans Chem Labs, Columbus, OH 43210 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 33期

关键词：

addition reactions; chelation; cyclohexanones; ethers; steric effects;

D O I：

10.1016/S0040-4039(99)01167-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereochemical course of the hydride reduction and of the 1,2-addition of allylmagnesium bromide as well as the Normant reagent to 1 has been determined. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5971 / 5974

页数：4

共 31 条

[1]

Anh N.T., 1980, TOP CURR CHEM, V88, P145

[2]

ANH NT, 1977, NOUV J CHIM, V1, P61

[3] STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUND ADDITION TO KETONES [J].

ASHBY, EC ;

LAEMMLE, JT .

CHEMICAL REVIEWS, 1975, 75 (04) :521-546

[4] Synthesis of myo-inositol 4,6-cyclic,1,5-trisphasphate, a conformationally restricted analogue of myo-inositol 1,4,5-trisphosphate [J].

Ballereau, S ;

Poirier, SN ;

Guillemette, G ;

Spiess, B ;

Schlewer, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (11) :1859-1864

[5]

CAHIEZ G, 1978, TETRAHEDRON LETT, P3013

[6]

CHEREST M, 1968, TETRAHEDRON LETT, P2205

[7]

CHEREST M, 1968, TETRAHEDRON LETT, P2199

[8] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT [J].

CIEPLAK, AS ;

TAIT, BD ;

JOHNSON, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8447-8462

[9]

CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041

[10] Isotopic perturbation of intramolecular hydrogen bonds in rigid 1,3-diols: NMR studies reveal unusually large equilibrium isotope effects [J].

Craig, BN ;

Janssen, MU ;

Wickersham, BM ;

Rabb, DM ;

Chang, PS ;

OLeary, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9610-9613

← 1 2 3 4 →