Analogies between Synthetic and Biosynthetic Reactions in Which [1,2]-Alkyl Shifts Are Combined with Other Events: Dyotropic, Schmidt, and Carbocation Rearrangements

被引：52
作者：
Gutierrez, Osvaldo [1 ]
Tantillo, Dean J. [1 ]
机构：
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 77卷 / 20期
基金：
美国国家科学基金会;
关键词：
SYMMETRY CONTROLLED REACTIONS; INDEPENDENT CHEMICAL-SHIFTS; LACTONES; AZIDES; CATION; STEREOSELECTIVITY; BUTYROLACTONES; CYCLOADDITION; CONSERVATION; CYCLIZATION;
D O I：
10.1021/jo301864h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A survey of computational studies on the mechanisms of dyotropic, Schmidt, and related reactions is presented. Connections between synthetically applied versions of these processes and those predicted to occur during biosynthetic terpene-forming carbocation cascades are highlighted.
引用
收藏
页码：8845 / 8850
页数：6
相关论文
共 80 条
[1]   Highly stereocontrolled synthesis of substituted propiolactones and butyrolactones from achiral lithium enolates and homochiral aldehydes [J].
Arrastia, I ;
Lecea, B ;
Cossio, FP .
TETRAHEDRON LETTERS, 1996, 37 (02) :245-248
[2]   INTRAMOLECULAR SCHMIDT REACTION OF ALKYL AZIDES [J].
AUBE, J ;
MILLIGAN, GL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (23) :8965-8966
[3]  
Beckmann E., 1886, Ber, V19, P988
[4]   What is a discovery? Carbon skeletal rearrangements as counter-examples to the rule of minimal structural change [J].
Berson, JA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (24) :4655-4660
[5]  
Birney DM, 2010, CURR ORG CHEM, V14, P1658
[6]   LACTONE SYNTHESIS VIA DYOTROPIC REARRANGEMENT - STEREOSPECIFIC CONSTRUCTION OF FUSED BUTYROLACTONES WITH 3 CONTIGUOUS ASYMMETRIC CENTERS [J].
BLACK, TH ;
DUBAY, WJ .
TETRAHEDRON LETTERS, 1988, 29 (15) :1747-1750
[7]   A UNIQUE 3-CHLOROBUTENOLIDE ANNULATION SEQUENCE [J].
BLACK, TH ;
MCDERMOTT, TS .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (03) :184-185
[8]   Verification of stereospecific dyotropic racemisation of enantiopure D and L-1,2-dibromo-1,2-diphenylethane in non-polar media [J].
Braddock, D. Christopher ;
Roy, Debjani ;
Lenoir, Dieter ;
Moore, Edward ;
Rzepa, Henry S. ;
Wu, Judy I-Chia ;
Schleyer, Paul von Rague .
CHEMICAL COMMUNICATIONS, 2012, 48 (71) :8943-8945
[9]   Dyotropic rearrangement of α-lactone to β-lactone:: a computational study of small-ring halolactonisation [J].
Buchanan, J. Grant ;
Ruggiero, Giuseppe D. ;
Williams, Ian H. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (01) :66-72
[10]   GEOMETRY OF MOLECULES .2. DIBORANE AND ETHANE [J].
BUENKER, RJ ;
PEYERIMHOFF, SD ;
ALLEN, LC ;
WHITTEN, JL .
JOURNAL OF CHEMICAL PHYSICS, 1966, 45 (08) :2835-+
12345678