2008
DOI: 10.1002/adsc.200800324
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Synthesis of Stereodefined Substituted Cycloalkenes by a One‐Pot Catalytic Boronation–Allylation–Metathesis Sequence

Abstract: Stereodefined cyclohexene and cyclopentene derivatives were prepared by the coupling of allylic alcohols and other allylic precursors with unsaturated aldehydes. These reactions are based on a multicatalytic one-pot approach involving palladium pincer complex-catalyzed boronation, allylation and ring-closing metathesis reactions. This reaction sequence can be performed in an operationally simple procedure affording the cycloalkene products in high overall yields and excellent regio-and stereoselectivities. The… Show more

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Cited by 23 publications
(17 citation statements)
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“…We were astonished to find that such an enantioselective allylation/RCM tandem process had never before been described in the literature, despite being two of the most reliable and widely used methodologies for C–C bond formation 21. Our challenge now was finding an allylation procedure which might be compatible with a subsequent RCM reaction.…”
Section: Chiral Brønsted Acid‐catalyzed Allylboration Reaction With Fmentioning
confidence: 99%
“…We were astonished to find that such an enantioselective allylation/RCM tandem process had never before been described in the literature, despite being two of the most reliable and widely used methodologies for C–C bond formation 21. Our challenge now was finding an allylation procedure which might be compatible with a subsequent RCM reaction.…”
Section: Chiral Brønsted Acid‐catalyzed Allylboration Reaction With Fmentioning
confidence: 99%
“…To alleviate some of the difficulty in preparing reactive allyl boronates for Petasis borono-Mannich reactions, Szabó and co-workers developed a method for the generation of an allyl boronate species in situ, which could be used directly as an allylating reagent. [15] Their group had previously shown the use of a selenium-based palladium pincer complex as an effective catalyst for the borylation of allylic alcohols. [16] A modified version of this catalyst, complex 27, was applied to generate the allyl boronate derivative of allylic alcohol 25 with diboronic acid (Scheme 10).…”
Section: Recent Examples Of Multicatalytic Reactionsmentioning
confidence: 99%
“…Application of 4-pentenal (7e) as aldehyde component in the one-pot coupling affords stereo-defined octadiene 8j, which subsequently can be cyclized in situ to the corresponding cyclohexene derivative 37 using Hoveyda-Grubbs catalyst 100,101 36 (eqn (12)). 16 This one-pot dicatalytic approach can be used for simple preparation of stereo-defined cyclohexenes (Table 10). The mild conditions and the compatibility of the palladium (1f) and ruthenium (36) catalysts with all reaction components allow a broad synthetic scope including silane (37a), benzyloxy (37b) and carbonyl (37d) derivatives.…”
Section: Ring Closing Metathesis Integrated In the Borylation Allylat...mentioning
confidence: 99%
“…Interesting to note is that cyclization of terminal trienes could also selectively be achieved (entry 3). 16 In this process only cyclohexene derivative 37c is formed without formation of a cycloheptenyl analogue. (12)…”
Section: Ring Closing Metathesis Integrated In the Borylation Allylat...mentioning
confidence: 99%
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