BF3•OEt2-Catalyzed Unexpected Stereoselective Formation of 2,4-trans-Diallyl-2-methyl-6-aryltetrahydro-2H-pyrans with Quaternary Stereocenters

被引：2

作者：

Reddy, D. Srinivas ^{[1
]}

Srinivas, Beduru ^{[1
]}

Rachineni, Kavitha ^{[2
]}

Jagadeesh, Bharatam ^{[2
]}

Sarotti, Ariel M. ^{[3
]}

Mohapatra, Debendra K. ^{[1
,4
]}

机构：

[1] CSIR Indian Inst Chem Technol, Dept Organ Synth & Proc Chem, Hyderabad 500007, India

[2] CSIR Indian Inst Chem Technol, Ctr NMR & Struct Chem, Hyderabad 500007, India

[3] Univ Nacl Rosario, Fac Ciencias Bioquim Farmaceut, Inst Quim Rosario CONICET, RA-2000 Rosario, Argentina

[4] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 09期

关键词：

CATALYTIC ASYMMETRIC ALLYLATION; NATURAL-PRODUCTS; REACTIVITY; RING; REARRANGEMENT; ANALOGS; ACID;

D O I：

10.1021/acs.joc.1c00352

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The present manuscript describes a convenient, mild, and highly stereoselective method for the allylation of delta-hydroxy-alpha,beta-unsaturated ketones having a benzylic hydroxyl group at the delta-position using allyltrimethylsilane mediated by BF3 center dot OEt2, leading to 2,4-diallyl-2-methyl-6-aryltetrahydro-2H-pyran ring systems with quaternary carbon stereogenic centers. This represents the first example of a tandem isomerization followed by one C-O and two C-C bond-forming reactions in one pot. The isolation of TMS-protected lactol as an intermediate from the reaction strongly supports the proposed mechanistic pathway.

引用

页码：6518 / 6527

页数：10

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