THE ASYMMETRIC-SYNTHESIS OF 2-BROMOHOMOALLYLIC ALCOHOLS USING THE TARTRATE ESTER OF (2-BROMOALLYL)BORONIC ACID PREPARED BY BROMOBORATION REACTION OF ALLENE

被引：0

作者：

HARA, S ^{[1
]}

YAMAMOTO, Y ^{[1
]}

FUJITA, A ^{[1
]}

SUZUKI, A ^{[1
]}

机构：

[1] OKAYAMA UNIV SCI,DEPT APPL CHEM,OKAYAMA 700,JAPAN

来源：

SYNLETT | 1994年 / 08期

关键词：

BROMOBORATION; TARTRATE ESTER; 2-BROMOALLYLBORANE; ASYMMETRIC SYNTHESIS; CHIRAL 2-BROMOHOMOALLYLIC ALCOHOLS;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral bis(2,4-dimethyl-3-pentyl)tartrate ester of (2-(2-bromoallyl)boronic acid was directly prepared from the corresponding bis(2,4-dimethyl-3-pentyl) tartrate and (2-bromoallyl)diisopropoxyborane (1), obtained by the bromoboration reaction of allene. The enantioselective synthesis of 2-bromohomoallylic alcohols was achieved using the chiral (2-bromoallyl)boranes.

引用

页码：639 / 640

页数：2

共 25 条

[1] THE ORGANIC-SYNTHESIS USING HALOBORATION REACTION .20. A SIMPLE SYNTHESIS OF (2-BROMOALLYL)DIPHENOXYBORANE BY THE BROMOBORATION OF ALLENE AND ITS REACTION WITH CARBONYL-COMPOUNDS
HARA, S
SUZUKI, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (46) : 6749 - 6752
[2] Synthesis of 4-(2-bromo-2-propenyl)-4-methyl-γ-butyrolactone by the reaction of ethyl levulinate with (2-bromoallyl)diisopropoxyborane prepared by haloboration of allene
Hara, S
Suzuki, A
[J]. ORGANIC SYNTHESES, VOL 75, 1998, 75 : 129 - 138
[3] ASYMMETRIC-SYNTHESIS USING TARTRATE ESTER MODIFIED ALLYLBORONATES .2. SINGLE AND DOUBLE ASYMMETRIC REACTIONS WITH ALKOXY-SUBSTITUTED ALDEHYDES
ROUSH, WR
HOONG, LK
PALMER, MAJ
STRAUB, JA
PALKOWITZ, AD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13): : 4117 - 4126
[4] VINYL ANION EQUIVALENT .5. ASYMMETRIC-SYNTHESIS OF ALLYLIC ALCOHOLS USING CHIRAL 2-(TRIALKYLSILYL)ETHYL SULFOXIDES
KUSUDA, S
UENO, Y
TORU, T
[J]. TETRAHEDRON, 1994, 50 (04) : 1045 - 1062
[5] ASYMMETRIC-SYNTHESIS USING CHIRAL PIPERAZINE .1. ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED ALCOHOL AND CARBOXYLIC-ACID BY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL DIAMIDES DERIVED FROM PIPERAZINES
SOAI, K
HAYASHI, H
SHINOZAKI, A
UMEBAYASHI, H
YAMADA, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) : 3450 - 3452
[6] ASYMMETRIC-SYNTHESIS USING THE BIS(2,4-DIMETHYL-3-PENTYL)-(L)-TARTRATE ESTERS OF SUBSTITUTED ALLYLBORONIC ACIDS - SYNTHESIS OF GAMMA,BETA-DISUBSTITUTED TETRAHYDROPYRANS AND TETRAHYDROFURANS
BROWN, HC
PHADKE, AS
[J]. SYNLETT, 1993, (12) : 927 - 928
[7] ASYMMETRIC-SYNTHESIS OF OPTICALLY-ACTIVE ALCOHOLS WITH 2 CHIRAL CENTERS FROM A RACEMIC ALDEHYDE BY THE SELECTIVE ADDITION OF DIALKYLZINC REAGENTS USING CHIRAL CATALYSTS
NIWA, S
HATANAKA, T
SOAI, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (08): : 2025 - 2027
[8] SYNTHESIS OF MALEIC ACID ESTERS BY ESTER INTERCHANGE OF DIMETHYL ESTER OF MALEIC ACID USING ALCOHOLS IN PRESENCE OF CATION-EXCHANGE RESIN WITH KU-2 RANK
ISAGULYA.VI
FEDOROVA, RI
GUDOK, ES
[J]. ZHURNAL PRIKLADNOI KHIMII, 1971, 44 (01) : 221 - +
[9] ADVANCES IN ELECTROORGANIC CHEMISTRY .2. DESIGN AND CONTROL OF NOVEL REACTION FIELDS AND REACTIVE SPECIES - ASYMMETRIC-SYNTHESIS USING MODIFIED ELECTRODE
TAKANO, N
[J]. DENKI KAGAKU, 1992, 60 (02): : 93 - 96
[10] STEREOCHEMISTRY OF P-CHIRAL PHOSPHINYLACETIC ACID ESTER .2. ASYMMETRIC-SYNTHESIS OF 4,4-DISUBSTITUTED ALKA-2,3-DIENOATES
MUSIEROWICZ, S
WROBLEWSKI, AE
[J]. TETRAHEDRON, 1980, 36 (10) : 1375 - 1380

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