Enantioselective total synthesis of (−)-Himalensine A via a palladium and 4-hydroxyproline co-catalyzed desymmetrization of vinyl-bromide-tethered cyclohexanones

Enantioselective total synthesis of (−)-Himalensine A via a palladium and 4-hydroxyproline co-catalyzed desymmetrization of vinyl-bromide-tethered cyclohexanones

Herein, we describe the convergent enantioselective total synthesis of himalensine A in 18 steps, enabled by a highly enantio- and diastereoselective construction of the morphan core via a palladium/hydroxy proline co-catalyzed desymmetrization of vinyl-bromide-tethered cyclohexanones. The reaction...

Mô tả đầy đủ

Chi tiết về thư mục
Những tác giả chính:	Kučera, R, Ellis, SR, Yamazaki, K, Hayward Cooke, J, Chekshin, N, Christensen, KE, Hamlin, TA, Dixon, DJ
Định dạng:	Journal article
Ngôn ngữ:	English
Được phát hành:	American Chemical Society 2023

Những quyển sách tương tự

Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones
Bằng: Zhang, L, et al.
Được phát hành: (2020)

Enantioselective silver and amine co-catalyzed desymmetrizing cycloisomerization of alkyne-linked cyclohexanones
Bằng: Manzano, R, et al.
Được phát hành: (2017)

Enantioselective desymmetrization of prochiral cyclohexanones by organocatalytic intramolecular Michael additions to α,β-unsaturated esters
Bằng: Gammack Yamagata, A, et al.
Được phát hành: (2015)

Palladium mediated enantioselective desymmetrization of meso 1,1-dihaloalkenes.
Bằng: Willis, M, et al.
Được phát hành: (2000)

Catalytic enantioselective nucleophilic desymmetrization of phosphonate esters
Bằng: Formica, M, et al.
Được phát hành: (2023)

A new organocatalytic desymmetrization reaction enables the enantioselective total synthesis of madangamine E
Bằng: Shiomi, S, et al.
Được phát hành: (2022)

Palladium-Catalyzed Conversion of Aryl and Vinyl Triflates to Bromides and Chlorides
Bằng: Shen, Xiaoqiang, et al.
Được phát hành: (2012)

Palladium-Catalyzed Conversion of Aryl and Vinyl Triflates to Bromides and Chlorides
Bằng: Pan, Jun, et al.
Được phát hành: (2013)

ORGN 743-Palladium-catalyzed enantioselective desymmetrization for the total synthesis of hodgkinsine and related structures
Bằng: Durbin, M, et al.
Được phát hành: (2006)

Total synthesis of (−)-himalensine A
Bằng: Shi, H, et al.
Được phát hành: (2017)

Enantioselective arylation and vinylation of allylic bromides catalyzed by guanidinium and copper(I) salt
Bằng: Jiang, Huan
Được phát hành: (2018)

Bifunctional iminophosphorane catalyzed amide enolization for enantioselective cyclohexadienone desymmetrization.
Bằng: Poh, CYX, et al.
Được phát hành: (2023)

Sequential desymmetrization-fluorination: enantioselective synthesis of fluorinated cyclitols.
Bằng: Purser, S, et al.
Được phát hành: (2006)

The determination of hydroxyproline /
Bằng: 350837 Neuman, Robert E., et al.

Second generation catalytic enantioselective nucleophilic desymmetrization at P(V): improved generality, efficiency and modularity
Bằng: Formica, M, et al.
Được phát hành: (2024)

Second generation catalytic enantioselective nucleophilic desymmetrization at P(V): improved generality, efficiency and modularity
Bằng: Formica, M, et al.
Được phát hành: (2024)

Palladium-catalyzed aerobic dehydrogenative aromatization of cyclohexanone imines to arylamines
Bằng: Hajra, Alakananda, et al.
Được phát hành: (2013)

Enantioselective desymmetrizing palladium catalyzed carbonylation reactions: the catalytic asymmetric synthesis of quaternary carbon center containing 1,3-dienes.
Bằng: Byrne, S, et al.
Được phát hành: (2010)

ORGN 134-Desymmetrization of bisvinyltriflates via palladium-catalyzed carbonylation
Bằng: Byrne, S, et al.
Được phát hành: (2006)

Bisguanidinium-catalyzed remote enantioselective desymmetrization with 1,2-acyl shift
Bằng: Chen, Wenchao, et al.
Được phát hành: (2024)

Functionalized bicyclo[3.3.0]octanes by enantioselective transannular desymmetrization.
Bằng: Hodgson, D, et al.
Được phát hành: (2001)

Asymmetric syntheses of (2R,3S)-3-hydroxyproline and (2S,3S)-3-hydroxyproline
Bằng: Davies, S, et al.
Được phát hành: (2018)

Enantioselective access to isoquinuclidines by tropenone desymmetrization and homoallylic radical rearrangement: synthesis of (+)-ibogamine.
Bằng: Hodgson, D, et al.
Được phát hành: (2005)

Palladium-Catalyzed Enantioselective α-Arylation and α-Vinylation of Oxindoles Facilitated by an Axially Chiral P-Stereogenic Ligand
Bằng: Taylor, Alexander M., et al.
Được phát hành: (2013)

The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates
Bằng: Cho, Eun Jin, et al.
Được phát hành: (2013)

Cyclohexanone and methylcyclohexanone/
Được phát hành: (1977)

A new reactivity pattern for vinyl bromides: cine-substitution via palladium catalysed C-N coupling/Michael addition reactions.
Bằng: Willis, M, et al.
Được phát hành: (2005)

Access to planar chiral ferrocenes via N-heterocyclic carbene-catalyzed enantioselective desymmetrization reactions
Bằng: Lv, Xiaokang, et al.
Được phát hành: (2022)

Palladium-Catalyzed Amination of Unprotected Five-Membered Heterocyclic Bromides
Bằng: Su, Mingjuan, et al.
Được phát hành: (2015)

Palladium catalysed enantioselective desymmetrisation of meso ditriflates.
Bằng: Willis, M, et al.
Được phát hành: (2002)

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides
Bằng: Milner, Phillip John, et al.
Được phát hành: (2017)

Palladium-Catalyzed Enantioselective α-Arylation of α-Fluoroketones
Bằng: Jiao, Zhiwei, et al.
Được phát hành: (2017)

Palladium catalysed enamine synthesis from vinyl triflates
Bằng: Willis, M, et al.
Được phát hành: (2002)

Total synthesis of (−)-himalensine A and development of novel C(sp3)-H functionalisation reactions
Bằng: Shi, H
Được phát hành: (2018)

Applications of planar-chiral phosphaferrocene-oxazolines in asymmetric catalysis and enantioselective desymmetrization by carbon nucleophiles in the presence of chiral ligands
Bằng: Shintani, Ryo, 1976-
Được phát hành: (2006)

Catalytic enantioselective intramolecular oxa-Michael reaction to α,β-unsaturated esters and amides
Bằng: Su, G, et al.
Được phát hành: (2023)

A General, Practical Palladium-Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides
Bằng: Senecal, Todd D., et al.
Được phát hành: (2015)

One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
Bằng: Davies, A, et al.
Được phát hành: (2016)

Palladium-Catalyzed Fluorination of Cyclic Vinyl Triflates: Effect of TESCF
Bằng: Ye, Yuxuan, et al.
Được phát hành: (2018)

Bifunctional iminophosphorane-catalyzed enantioselective sulfa-michael addition to unactivated α,β-unsaturated amides
Bằng: Rozsar, D, et al.
Được phát hành: (2022)