Experimental and Computational Studies of the Diastereoselective Alkylations of 3-Substituted γ-Sultams

被引：4

作者：

Fauber, Benjamin P. ^{[1
]}

Clagg, Kyle ^{[1
]}

Gibbons, Paul ^{[1
]}

Rene, Olivier ^{[1
]}

机构：

[1] Genentech Inc, Discovery Chem, San Francisco, CA 94080 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 01期

关键词：

ALPHA-SULFONYL CARBANIONS; RAY CRYSTAL-STRUCTURE; ELECTROPHILIC SUBSTITUTION; SATURATED CARBON; LITHIUM-SALTS; AB-INITIO; STEREOCHEMISTRY; 1,3-DITHIANES; SULFONAMIDES; REACTIVITY;

D O I：

10.1021/jo502506j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report that chiral 3-substituted gamma-sultam alpha-carbanions undergo diastereoselective alkylation reactions with alkyl halides to predominantly produce trans-3,5-disubstituted gamma-sultam products. Quantum mechanical calculations provided a stereoelectronic rationale for the observed diastereoselectivity.

引用

页码：685 / 689

页数：5

共 50 条

[21] Diastereoselective addition of organocerium(III) reagents derived from 3-substituted propargyl bromides to aldehydes
Groth, Ulrich
Kesenheimer, Christian
Neidhoefer, Juerger
SYNLETT, 2006, (12) : 1859 - 1862
[22] Enantio- and Diastereoselective Organocatalytic α-Alkylation of Aldehydes with 3-Substituted 2-(Bromomethyl)acrylates
Jimenez, Jacqueline
Landa, Aitor
Lizarraga, Aitziber
Maestro, Miguel
Mielgo, Antonia
Oiarbide, Mikel
Velilla, Irene
Palomo, Claudio
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (01): : 747 - 753
[23] Pd-Catalyzed Asymmetric Allylic Alkylations of 3-Substituted Indoles Using Chiral P/Olefin Ligands
Liu, Yilin
Du, Haifeng
ORGANIC LETTERS, 2013, 15 (04) : 740 - 743
[24] THE IONIZATION CONSTANTS OF 3-SUBSTITUTED PYRIDINES, 3-SUBSTITUTED QUINOLINES AND 4-SUBSTITUTED ISOQUINOLINES
BRYSON, A
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (18) : 4871 - 4876
[25] Studies on agarofurans - III. The synthesis of 3-substituted agarofurans
Zhang, WY
Guo, JY
Liang, XT
CHINESE CHEMICAL LETTERS, 2000, 11 (04) : 301 - 304
[26] STUDIES OF THE FORMATION AND STABILITY OF PENTADIENYL AND 3-SUBSTITUTED PENTADIENYL RADICALS
CLARK, KB
CULSHAW, PN
GRILLER, D
LOSSING, FP
SIMOES, JAM
WALTON, JC
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (19): : 5535 - 5539
[27] SYNTHESIS AND STUDIES OF SOME NEW 3-SUBSTITUTED COUMARIN DERIVATIVES
IBRAHIM, TM
AHMED, FSM
SHEDID, SA
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 86 (1-4): : 263 - 268
[28] Synthesis and receptor binding studies of 3-substituted piperazine derivatives
Bedürftig, S
Wünsch, B
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (03) : 387 - 396
[29] STUDIES ON ISOXAZOLES .6. ON THE SYNTHESIS OF 3-SUBSTITUTED ISOXAZOLES
KOCHETKOV, NK
KHORLIN, AY
ZHURNAL OBSHCHEI KHIMII, 1958, 28 (07): : 1937 - 1940
[30] 3-SUBSTITUTED TROPANE DERIVATIVES .3. 3-SUBSTITUTED TROPANE CARBINOLS, ALKENES, AND ALKANES
ZIRKLE, CL
INDIK, ZK
ANDERSON, EL
CRAIG, PN
PAVLOFF, AM
GERNS, FR
JOURNAL OF MEDICINAL CHEMISTRY, 1962, 5 (02) : 341 - &

← 1 2 3 4 5 →