The DAI Research Group at HKUST


 

Professor Wei-Min DAI  (PhD, Kyoto, 1990)
Professor of Chemistry

E-mail:chdai@ust.hk        
Tel: (852) 2358-7365        
Fax: (852) 2358-1594

ResearcherID: B-6981-2008
ORCID: 0000-0001-5688-7606
HKUST Scholarly Publications [enter
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(Last updated: 2 September 2017) 


Research Interests: Synthetic organic and bioorganic chemistry

Prof. Dai's research focuses on two directions: chirality & catalysis, and synthesis of bioactive molecules including diverted total synthesis of natural products.

Our contributions to chirality & catalysis include: (1) development of indole-containing chiral molecules from abrine for enantioselective alkylation of aldehydes with diethylzinc; (2) asymmetric Wittig-type olefinations of chiral arsonium ylides with 4-substituted cyclohexanones and N,N-dialkyl 2-formyl-1-naphthamides; (3) remote axial-to-central chirality transfer in SmI2-mediated enantioselective reductive coupling of 1-naphthamide-derived axially chiral crotonates with aliphatic aldehydes; (4) Pd-catalyzed asymmetric allylic alkylation (AAA), asymmetric Heck reaction, and asymmetric SuzukiMiyaura cross-coupling reaction using novel atropisomeric amide-derived phosphanes (A˛phos), C2-symmetric chiral arsines, and P-chiral secondary phosphane oxides; (5) generation of aromatic amide-derived phosphane (Aphos) ligands via “Self-Assisted Molecular Editing” (SAME) protocol for room temperature SuzukiMiyaura cross-coupling of unactivated and sterically hindered aryl chlorides under mild basic conditions; and (6) development of Pd(OAc)2Aphos-Y catalyst system for B-alkyl SuzukiMiyaura cross-coupling of alkenyl halides an alternative to Pd(dppf)Cl2AsPh3 commonly used in total synthesis; (7) demonstration of an integrative approach of microwave-assisted solid-phase organic synthesis (MASPOS) with encoded split-pool combinatorial synthesis (ESPCS) as illustrated in Cu-mediated heteroannulation for synthesis of indoles; and (8) the first introduction of the cat·linker concept for promoting on-resin metal-catalyzed reactions.

Our accomplishments in synthesis of bioactive molecules cover: (1) total synthesis of amphidinolide X and Y via a ring-closing metathesis (RCM) approach toward formation of the (E)-trisubstituted alkene; (2) diverted total synthesis of amphidinolide T1–T5 and amphidinin B via a RCM–asymmetric dihydroxylation (RCM–AD) sequence starting from an advanced common intermediate which was designed according to a complexity-based planning strategy; (3) total synthesis of 24-demethylbafilomycins using a novel diester-tethered 1,3-dieneene RCM; (4) diverted total synthesis and stereochemistry determination of marine butenolides using a three-module assembly approach; (5) diverted total synthesis of diastereoisomers of iriomoteolide-1a and -1b using a four-module assembly approach; (6) total synthesis of the fully functionalized mycolactone core via a relay RCM (RRCM) strategy and total synthesis of mycolactone E; (7) diverted total synthesis of ()-palmyrolide A and its 5,7-epimer and four diastereoisomers of laingolide A using Pd(OAc)2Aphos-Y-catalyzed "9-MeO-9-BBN variant" of B-alkyl Suzuki-Miyaura cross-coupling and RCM/isomerization as the key steps, and determination of the relative configuration of laingolide A; (8) diverted total synthesis of diastereoisomers of laingolide and determination of its relative configuration using a multimodule assembly approach; (9) total synthesis of diastereomers of amphidinolactone B using a multimodule assembly approach; (10) establishment of an allylic rearrangement strategy for in situ formation of 10-membered ring enediynes with promising DNA cleavage and anticancer activity; and (11) development of a number of synthetic methodologies for diversity-oriented synthesis of privileged heterocyclic scaffolds via microwave-assisted multicomponent reactions and post annulation.

Selected Ongoing Projects:

Selected Journal Publications:    [see more entries]

Chirality & Catalysis:

Total Synthesis and Diverted Total Synthesis:

Microwave-Assisted & Diversity-Oriented Organic Synthesis:

Microwave-Assisted Solid-Phase Organic Synthesis (MASPOS):

Designed Enediyne Prodrugs:

Selected Conference Presentations:    [see more entries]

Selected Seminars on Diverted Total Synthesis:

Recent PhD Theses:    [see more entries]