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David W. Old

Massachusetts Institute of Technology

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Angewandte Chemie | 1999

Total Synthesis of (±)-Gelsemine

Andrew Madin; Christopher J. O'Donnell; Taeboem Oh; David W. Old; Larry E. Overman; Matthew J. Sharp

A complex molecular reorganization (1-->2), a sequential anionic aza-Cope rearrangement and Mannich cyclization, and an unprecedented intramolecular Heck reaction of the tetrasubstituted double bond of a vinylogous carbamate are key steps in a new total synthesis of (+/-)-gelsemine (3). MOM=methoxymethyl, DBU=1,8-diazabicyclo[5.4.0]undec-7-ene.

Angewandte Chemie | 1999

TOTALSYNTHESE VON ()-GELSEMIN

Andrew Madin; Christopher J. O'Donnell; Taeboem Oh; David W. Old; Larry E. Overman; Matthew J. Sharp

Eine komplexemolekulareReorganisation (1→2), eine Sequenz aus Aza-Cope-Umlagerung und Mannich-Cyclisierung und eine neuartige intramolekulare Heck-Reaktion der tetrasubstituierten Doppelbindung eines vinylogen Carbamats sind die Schlusselschritte einer neuen Totalsynthese von (±)-Gelsemin 3. MOM=Methoxymethyl, DBU=1,8-Diazabicyclo[5.4.0]undec-7-en.

Journal of the American Chemical Society | 1998

A Highly Active Catalyst for Palladium-Catalyzed Cross-Coupling Reactions: Room-Temperature Suzuki Couplings and Amination of Unactivated Aryl Chlorides

David W. Old; John P. Wolfe; Stephen L. Buchwald

Journal of the American Chemical Society | 1999

Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers

Attila Aranyos; David W. Old; Ayumu Kiyomori; John P. Wolfe; and Joseph P. Sadighi; Stephen L. Buchwald

Organic Letters | 2000

Efficient Palladium-Catalyzed N-Arylation of Indoles

David W. Old; and Michele C. Harris; Stephen L. Buchwald

Journal of the American Chemical Society | 2005

Use of the Intramolecular Heck Reaction for Forming Congested Quaternary Carbon Stereocenters. Stereocontrolled Total Synthesis of (±)-Gelsemine

Andrew Madin; Christopher J. O'Donnell; Taeboem Oh; David W. Old; Larry E. Overman; Matthew J. Sharp

Journal of the American Chemical Society | 2005

Aza-Cope Rearrangement-Mannich Cyclizations for the Formation of Complex Tricyclic Amines: Stereocontrolled Total Synthesis of (±)-Gelsemine

W. G. Earley; Jacobsen Je; Andrew Madin; Meier Gp; Christopher J. O'Donnell; Taeboem Oh; David W. Old; Larry E. Overman; Matthew J. Sharp

Archive | 1999

Ligands for metals and metal-catalyzed processes

Stephen L. Buchwald; David W. Old; John P. Wolfe; Michael Palucki; Ken Kamikawa; Andrew Chieffi; Joseph P. Sadighi; Robert A. Singer; Jens Ahman

e-EROS Encyclopedia of Reagents for Organic Synthesis | 2011

2‐(Di‐tert‐butylphosphino)biphenyl

John P. Wolfe; David W. Old

e-EROS Encyclopedia of Reagents for Organic Synthesis | 2009

2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl

John P. Wolfe; David W. Old

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