CsF in organic synthesis.: Regioselective nucleophilic reactions of phenols with oxiranes leading to enantiopure β-blockers

被引：56

作者：

Kitaori, K

Furukawa, Y

Yoshimoto, H

Otera, J

机构：

[1] Daiso Co Ltd, Res Labs, Amagasaki, Hyogo 6600842, Japan

[2] Okayama Univ Sci, Dept Appl Chem, Okayama 7000005, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 50期

关键词：

D O I：

10.1016/S0040-4020(99)00896-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

The two modes of the paths in the reaction of oxiranes with phenols are completely controlled by CsF. Glycidyl nosylate undergoes exclusive substitution at the C-1 position whereas the ring-opening (C-3 attack) occurs with epichlorohydrin, glycidol, and 1,2-epoxyalkanes. These reactions provide convenient access to enantiopure beta-blockers. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：14381 / 14390

页数：10

相关论文

共 35 条

[1]

ENZYME ASSISTED PREPARATION OF ENANTIOMERICALLY PURE BETA-ADRENERGIC BLOCKERS .3. OPTICALLY-ACTIVE CHLOROHYDRIN DERIVATIVES AND THEIR CONVERSION [J].

ADER, U ;

SCHNEIDER, MP .

TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :521-524

[2]

AN EFFICIENT SYNTHESIS OF (R)-(+)-PROPRANOLOL AND (S)-(-)-PROPRANOLOL FROM RESOLVED 5-IODOMETHYLOXAZOLIDIN-2-ONES [J].

CARDILLO, G ;

ORENA, M ;

SANDRI, S ;

TOMASINI, C .

TETRAHEDRON, 1987, 43 (11) :2505-2512

[3]

TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].

CARON, M ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560

[4]

A PRACTICAL SYNTHETIC ROUTE TO ENANTIOPURE 3-ARYLOXY-1,2-PROPANEDIOLS FROM CHIRAL GLYCIDOL [J].

CHEN, JA ;

SHUM, W .

TETRAHEDRON LETTERS, 1995, 36 (14) :2379-2380

[5]

FUJI M, 1992, CHEM PHARM BULL, V40, P2353

[6]

REGIOSPECIFIC OPENING OF GLYCIDYL DERIVATIVES MEDIATED BY BORON-TRIFLUORIDE - ASYMMETRIC-SYNTHESIS OF ETHER-LINKED PHOSPHOLIPIDS [J].

GUIVISDALSKY, PN ;

BITTMAN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4637-4642

[7]

MILD, EFFICIENT AND SELECTIVE OPENING OF EPOXIDES WITH ALCOHOLS CATALYZED BY CERIC(IV) AMMONIUM-NITRATE [J].

IRANPOOR, N ;

BALTORK, IM .

SYNTHETIC COMMUNICATIONS, 1990, 20 (18) :2789-2797

[8]

A NEW, GENERAL ENTRY TO 4-SUBSTITUTED INDOLES - SYNTHESIS OF (S)-(-)-PINDOLOL AND (+/-)-CHUANGXINMYCIN [J].

ISHIBASHI, H ;

TABATA, T ;

HANAOKA, K ;

IRIYAMA, H ;

AKAMATSU, S ;

IKEDA, M .

TETRAHEDRON LETTERS, 1993, 34 (03) :489-492

[9]

ISHIBASHI H, 1994, CHEM PHARM BULL, V42, P271

[10]

Kitaori K, 1998, SYNLETT, P499

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