First example of memory of chirality in carbenium ion chemistry

被引：60

作者：

Matsumura, Y ^{[1
]}

Shirakawa, Y ^{[1
]}

Satoh, Y ^{[1
]}

Umino, M ^{[1
]}

Tanaka, T ^{[1
]}

Maki, T ^{[1
]}

Onomura, O ^{[1
]}

机构：

[1] Nagasaki Univ, Fac Pharmaceut Sci, Nagasaki 8528521, Japan

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 12期

关键词：

D O I：

10.1021/ol005795t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The non-Kolbe reaction of N-benzoyloxazolidine derivatives 6 derived from L-serine gave optically active N,O-acetals 7 when graphite was used as an anode material, This reaction represents the first example of "memory of chirality" in carbenium ion chemistry, The material used for the anode was critical for the memory of chirality, The substitution of carboxyl group with methoxyl group was found to proceed with an inversion mechanism.

引用

页码：1689 / 1691

页数：3

共 15 条

[1] BAIZER MM, 1991, ORGANIC ELECTROCHEMI, pCH30
[2] A CYCLIZATION REACTION OF METHYL (4R)-3-(2-DIAZO-3-OXOBUTANOYL)THIAZOLIDINE-4-CARBOXYLATE WHICH PROCEEDS WITH RETENTION OF CONFIGURATION, PROBABLY VIA A PLANAR ESTER ENOLATE INTERMEDIATE POSSESSING AXIAL CHIRALITY
BEAGLEY, B
BETTS, MJ
PRITCHARD, RG
SCHOFIELD, A
STOODLEY, RJ
VOHRA, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) : 924 - 925
[3] Fuji K, 1998, CHEM-EUR J, V4, P373, DOI 10.1002/(SICI)1521-3765(19980310)4:3<373::AID-CHEM373>3.0.CO
[4] 2-O
[5] THE SYNTHESIS AND CONFIGURATIONAL STABILITY OF DIFFERENTIALLY PROTECTED BETA-HYDROXY-ALPHA-AMINO ALDEHYDES
GARNER, P
PARK, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (12) : 2361 - 2364
[6] AN UNUSUAL REARRANGEMENT OF A LITHIATED N-ACYL-TETRAHYDROISOQUINOLINE TO AN AMINO-INDAN SKELETON AND STRUCTURAL COMPARISON OF 3-AMINO-2-METHYLINDAN ACIDS AND TETRAHYDRONAPHTHALENE-2-CARBOXYLIC ACIDS AS POSSIBLE BUILDING-BLOCKS FOR PEPTIDE-TURN MIMICS
GEES, T
SCHWEIZER, WB
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1993, 76 (07) : 2640 - 2653
[7] ELECTROCHEMICAL SYNTHESIS OF SEMICYCLIC AND CYCLIC N-ACYL N,O-ACETALS
IWASAKI, T
HORIKAWA, H
MATSUMOTO, K
MIYOSHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) : 1552 - 1554
[8] DIRECT ASYMMETRIC ALPHA-ALKYLATION OF PHENYLALANINE DERIVATIVES USING NO EXTERNAL CHIRAL SOURCES
KAWABATA, T
WIRTH, T
YAHIRO, K
SUZUKI, H
FUJI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) : 10809 - 10810
[9] MEMORY OF CHIRALITY - ENANTIOSELECTIVE ALKYLATION REACTIONS AT AN ASYMMETRIC CARBON ADJACENT TO A CARBONYL GROUP
KAWABATA, T
YAHIRO, K
FUJI, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) : 9694 - 9696
[10] ANODIC OXIDATIONS .5. KOLBE OXIDATION OF PHENYLACETIC ACID AND 1-METHYLCYCLOHEXANEACETIC ACID AT PLATINUM AND AT CARBON
ROSS, SD
FINKELST.M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (10) : 2923 - &

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