Enantioselective synthesis of isochromans and tetrahydroisoquinolines by C-H insertion of donor/donor carbenes

被引：31

作者：

Nickerson, Leslie A. ^{[1
]}

Bergstrom, Benjamin D. ^{[1
]}

Gao, Mingchun ^{[1
]}

Shiue, Yuan-Shin ^{[1
]}

Laconsay, Croix J. ^{[1
]}

Culberson, Matthew R. ^{[1
]}

Knauss, Walker A. ^{[1
]}

Fettinger, James C. ^{[1
]}

Tantillo, Dean J. ^{[1
]}

Shaw, Jared T. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, One Shields Ave, Davis, CA 95616 USA

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 02期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

RHODIUM CARBENOIDS; DONOR; DONOR/ACCEPTOR; MECHANISM; CATALYST; STEVENS;

D O I：

10.1039/c9sc05111b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reports of C-H insertions forming six-membered rings containing heteroatoms are rare due to Stevens rearrangements occurring after nucleophilic attack on the carbene by a heteroatom. Using donor/donor carbenes and Rh-2(R-PTAD)(4) as a catalyst, we have synthesized a collection of isochroman substrates in good yield, with excellent diastereo- and enantioselectivity, and no rearrangement products were observed. Furthermore, we report the first synthesis of six-membered rings containing nitrogen by C-H insertion to form tetrahydroisoquinolines. In one case, a Stevens rearrangement product was isolated at elevated temperature from a carbamate-protected amine substrate and computational evidence suggests formation through a free ylide not bound to rhodium.

引用

页码：494 / 498

页数：5

共 50 条

[21] Catalytic and enantioselective allylic C-H activation with donor-acceptor-substituted carbenoids
Davies, HML
Nikolai, J
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (23) : 4176 - 4187
[22] CpxM(iii)-catalyzed enantioselective C-H functionalization through migratory insertion of metal-carbenes/nitrenes
Pan, Chongqing
Yin, Si-Yong
Gu, Qing
You, Shu-Li
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (34) : 7264 - 7275
[23] CpxM(iii)-catalyzed enantioselective C-H functionalization through migratory insertion of metal-carbenes/nitrenes
Pan, Chongqing
Yin, Si-Yong
Gu, Qing
You, Shu-Li
Organic and Biomolecular Chemistry, 2021, 19 (34): : 7264 - 7275
[24] Silver-Catalyzed C-H Insertion Reactions with Donor-Acceptor Diazoacetates
Lovely, Carl J.
Flores, Jaime A.
Meng, Xiaofeng
Dias, H. V. Rasika
SYNLETT, 2009, (01) : 129 - 132
[25] Key Selectivity Controlling Elements in Rhodium-Catalyzed C-H Functionalization with Donor/Acceptor Carbenes
Ren, Zhi
Musaev, Djamaladdin G.
Davies, Huw M. L.
ACS CATALYSIS, 2022, 12 (21) : 13446 - 13456
[26] Guiding principles for site selective and stereoselective intermolecular C-H functionalization by donor/acceptor rhodium carbenes
Davies, Huw M. L.
Morton, Daniel
CHEMICAL SOCIETY REVIEWS, 2011, 40 (04) : 1857 - 1869
[27] Stereoelectronic Effect for the Selectivity in C-H Insertion of Alkylidene Carbenes and Its Application to the Synthesis of Platensimycin
Yun, Sang Young
Zheng, Jun-Cheng
Lee, Daesung
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) : 8413 - +
[28] Intermolecular C-H insertions of donor/acceptor-substituted rhodium carbenoids: A practical solution for catalytic enantioselective C-H activation
Davies, HML
Loe, O
SYNTHESIS-STUTTGART, 2004, (16): : 2595 - 2608
[29] Enantioselective synthesis of Bakuchiol using diazosulfonate C-H insertion to install the quaternary center
Bequette, Joseph P.
Jungong, Christian S.
Novikov, Alexei V.
TETRAHEDRON LETTERS, 2009, 50 (50) : 6963 - 6964
[30] Enantioselective intramolecular C-H insertion route to a key intermediate for the synthesis of trinem antibiotics
Anada, M
Hashimoto, S
TETRAHEDRON LETTERS, 1998, 39 (49) : 9063 - 9066

← 1 2 3 4 5 →