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

[1] Asymmetric synthesis of 3-substituted γ- and δ-sultams
Enders, D
Moll, A
Bats, JW
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) : 1271 - 1284
[2] Efficient asymmetric synthesis of 3-substituted β-sultams
Enders, D
Wallert, S
TETRAHEDRON LETTERS, 2002, 43 (29) : 5109 - 5111
[3] Highly diastereoselective alkylation of 3-substituted tetrahydroisoquinolines
Monsees, A
Laschat, S
Dix, I
Jones, PG
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26): : 10018 - 10021
[4] STUDIES ON 3-SUBSTITUTED CYCLOPENTANOLS
FUCHS, B
HABER, RG
BULLETIN OF THE RESEARCH COUNCIL OF ISRAEL, 1962, A 11 (01): : 30 - &
[5] A Computational Determination of the Origins of Diastereoselective Alkylations of a Cysteinesulfenate Anion
Schwan, Adrian L.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (2-3) : 519 - 526
[6] Lipase-mediated diastereoselective and enantioselective acetylations of 3-substituted cyclohexanols
Tanikaga, R
Morita, A
TETRAHEDRON LETTERS, 1998, 39 (07) : 635 - 638
[7] Lipase-mediated diastereoselective and enantioselective acetylations of 3-substituted cyclohexanols
Tanikaga, R.
Morita, A.
Tetrahedron Letters, 39 (07):
[8] 3-Substituted xanthines as promising candidates for quadruplex formation: computational, synthetic and analytical studies
Szolomajer, Janos
Paragi, Gabor
Batta, Gyula
Guerra, Celia Fonseca
Bickelhaupt, F. Matthias
Kele, Zoltan
Padar, Petra
Kupihar, Zoltan
Kovacs, Lajos
NEW JOURNAL OF CHEMISTRY, 2011, 35 (02) : 476 - 482
[9] DIASTEREOSELECTIVE SYNTHESIS OF CIS-2,3-SUBSTITUTED OR TRANS-2,3-SUBSTITUTED TETRAHYDROFURANS AND 3,4-SUBSTITUTED 4-BUTANOLIDES
FRAUENRATH, H
PHILIPPS, T
LIEBIGS ANNALEN DER CHEMIE, 1985, (10): : 1951 - 1961
[10] A highly diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives
Allin, SM
Northfield, CJ
Page, MI
Slawin, AMZ
TETRAHEDRON LETTERS, 1999, 40 (01) : 143 - 146

← 1 2 3 4 5 →