An Efficient [4 + 2 + 1] Entry to Seven-Membered Rings
- 20 August 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (36) , 11162-11163
- https://doi.org/10.1021/ja046147y
Abstract
A new nickel-catalyzed procedure for the [4 + 2 + 1] cycloaddition of trimethylsilyl diazomethane with alkynes tethered to dienes has been developed. A broad range of unsaturated substrates participate in the sequence, and stereoselectivities are generally excellent. Three possible mechanisms are proposed, and each involves the generation of a transient nickel carbene species.Keywords
This publication has 30 references indexed in Scilit:
- Rhodium-Catalyzed Novel Carbonylative Carbotricyclization of EnediynesJournal of the American Chemical Society, 2000
- Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement SequenceThe Journal of Organic Chemistry, 1999
- Diastereoselective Synthesis of cis-1,2-Dialkenylcyclopropanols and Subsequent Oxy-Cope RearrangementJournal of the American Chemical Society, 1995
- Metal-promoted higher-order cycloaddition reactions. Stereochemical, regiochemical, and mechanistic aspects of the [6.pi. + 4.pi.] reactionJournal of the American Chemical Society, 1993
- Cyclopropylcarbene-tungsten complexes + alkynes: a [4 + 2 + 1] cycloaddition route for the construction of seven-membered ringsJournal of the American Chemical Society, 1991
- Transition metal template controlled cycloaddition reactions. An efficient chromium(0)-mediated [6.pi. + 2.pi.] cycloadditionJournal of the American Chemical Society, 1991
- Cyclization reactions of a molybdenum carbene complex with 1,3-nonadien-8-ynesJournal of the American Chemical Society, 1991
- Rhodium(II)-catalyzed cyclization reactions of alkynyl-substituted .alpha.-diazo ketonesThe Journal of Organic Chemistry, 1991
- Scope and stereochemistry of the tandem intramolecular cyclopropanation/Cope rearrangement sequenceThe Journal of Organic Chemistry, 1989
- A facile route to divinylcyclopropanes. An efficient method for the annelative formation of functionalized cycloheptanesThe Journal of Organic Chemistry, 1976