(S)-(-)-2-TERT-BUTYL-3-METHYLENE-OXIRANE - SYNTHESIS AND HYDROBORATION OF A CHIRAL ALLENE OXIDE

被引：18

作者：

KONOIKE, T

HAYASHI, T

ARAKI, Y

机构：

[1] Shionogi Research Laboratories, Shionogi and Co., Ltd., Fukushima-ku, Osaka

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80126-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The chiral allene oxide, (S)-(-)-2-tert-butyl-3-methylene-oxirane 12 ((S)-(-)-1-tert-butylallene oxide) was prepared in a moderate yield and in high enantiomeric excess by a three-step conversion starting from 4,4-dimethyl-2-pentyn-1-ol 6. The procedure was comprised of hydrostannylation, Sharpless epoxidation and deoxystannylation. The chiral allene oxide 12 has moderate stability for identification and characterization and undergoes hydroboration to afford a chiral diol, (R)4,4-dimethylpentane-1,3-diol 15.

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页码：1559 / 1566

页数：8

相关论文

共 25 条

[1] CHEMISTRY OF ALLENE OXIDES .5. [J].

CHAN, TH ;

ONG, BS .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (15) :2994-3001

[2] TETRAHEDRON REPORT .91. CHEMISTRY OF ALLENE OXIDES [J].

CHAN, TH ;

ONG, BS .

TETRAHEDRON, 1980, 36 (16) :2269-2289

[3] OXIDATIVE CYCLIZATIONS OF ALLENIC ALDEHYDES [J].

CRANDALL, JK ;

RAMBO, E .

TETRAHEDRON LETTERS, 1994, 35 (10) :1489-1492

[4] 1,4-DIOXASPIRO[2.2]PENTANES - SYNTHESIS, SPECTROSCOPIC PROPERTIES, AND REACTIONS WITH NUCLEOPHILES [J].

CRANDALL, JK ;

BATAL, DJ ;

SEBESTA, DP ;

LIN, F .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1153-1166

[5] REACTION OF ORGANOTIN HYDRIDES WITH ACETYLENIC ALCOHOLS [J].

ENSLEY, HE ;

BUESCHER, RR ;

LEE, K .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :404-408

[6] CHEMISTRY OF SINGLET OXYGEN - ISOLATION AND CHARACTERIZATION OF A STABLE ALLENE OXIDE FROM A FULVENE ENDOPEROXIDE [J].

ERDEN, I ;

DRUMMOND, J ;

ALSTAD, R ;

XU, FP .

TETRAHEDRON LETTERS, 1993, 34 (08) :1255-1258

[7] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].

GAO, Y ;

HANSON, RM ;

KLUNDER, JM ;

KO, SY ;

MASAMUNE, H ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780

[8] HIGHLY ENANTIOSELECTIVE SYNTHESIS OF ALPHA-FLUORO KETONES VIA ALLENE OXIDES [J].

KABAT, MM .

TETRAHEDRON-ASYMMETRY, 1993, 4 (07) :1417-1420

[9]

KABAT MM, 1993, TETRAHEDRON LETT, V34, P843

[10] NEW REAGENTS .24. NEW POSSIBLE APPLICATIONS OF HEAVY MAIN-GROUP ELEMENTS IN ORGANIC-SYNTHESIS [J].

KAUFFMANN, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (06) :410-429