A HIGHLY STEREOSELECTIVE PREPARATION OF A NOVEL CLASS OF VINYL EPOXIDES FROM ALPHA-ALLENIC ALCOHOLS

被引：28

作者：

FRIESEN, RW

BLOUIN, M

机构：

[1] Merck Frosst Centre for Therapeutic Research, Quebec, H9R 4P8, P.O. Box 1005, Pointe Claire-Dorval

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 07期

关键词：

D O I：

10.1021/jo00059a006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of alpha-allenic alcohols 1 with iodine provides a mixture of Z- and E-diiodides 2 and 3, respectively. When treated with base, the diiodides are efficiently converted in a highly diastereoselective manner into the trans-iodovinyl epoxides 4.

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页码：1653 / 1654

页数：2

相关论文

共 26 条

[1] CONVERSION OF KETONES INTO VINYL-OXIRANES [J].

COOKSON, RC ;

CRUMBIE, RL .

TETRAHEDRON LETTERS, 1985, 26 (28) :3377-3380

[2] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+

[3] ALLENES .24. PREPARATION OF ALPHA-ALLENIC ALCOHOLS FROM MONO-O-TETRAHYDROPYRAN-2-YL DERIVATIVES OF BUTYNE-1,4-DIOLS [J].

COWIE, JS ;

LANDOR, PD ;

LANDOR, SR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (07) :720-724

[4]

DANG HS, 1992, TETRAHEDRON LETT, V33, P6169

[5] A HIGHLY STEREOSELECTIVE CONVERSION OF ALPHA-ALLENIC ALCOHOLS TO 1,2-SYN AMINO ALCOHOL DERIVATIVES VIA IODOCARBAMATION [J].

FRIESEN, RW .

TETRAHEDRON LETTERS, 1990, 31 (30) :4249-4252

[6] IODOCYCLIZATION OF THE (TOLYLSULFONYL)CARBAMATES AND (TRICHLOROACETYL)CARBAMATES OF SECONDARY ALPHA-ALLENIC ALCOHOLS - HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF SYN-1,2-AMINO ALCOHOLS AND TRANS-5-ALKYL-2-OXO-OXAZOLIDINE-4-CARBOXYLIC ACIDS [J].

FRIESEN, RW ;

KOLACZEWSKA, AE .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (16) :4888-4895

[7]

FRIESEN RW, 1991, SYNLETT, P420

[8] SELECTIVE CONDENSATION OF [3-(ALKYLTHIO)ALLYL]TITANIUM REAGENT WITH CARBONYL-COMPOUNDS [J].

FURUTA, K ;

IKEDA, Y ;

MEGURIYA, N ;

IKEDA, N ;

YAMAMOTO, H .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2781-2790

[9]

HUDLICKY T, 1991, COMPREHENSIVE ORGANI, V5

[10] SELECTIVE COUPLING OF [(ALKYLTHIO)ALLYL]TITANIUM REAGENT WITH CARBONYL-COMPOUNDS - FACILE ENTRY TO ALKENYL OXIRANES AND 2-(ARYLTHIO)-1,3-BUTADIENES [J].

IKEDA, Y ;

FURUTA, K ;

MEGURIYA, N ;

IKEDA, N ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (26) :7663-7665