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B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones.
Org Lett. 2006 Aug 31; 8(18):4089-91.OL

Abstract

Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(gamma-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and alpha-silylallenyl 3-degree-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic alpha-hydroxy acids and gamma-bromopropynyl carbinols, respectively.

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Authors+Show Affiliations

Hernandez E
University of Puerto Rico, Department of Chemistry, Rio Piedras, PR 00931-3346, USA.
Burgos CH
No affiliation info available
Alicea E
No affiliation info available
Soderquist JA
No affiliation info available

MeSH

AlkanesAlkynesCatalysisKetonesMethanolMolecular StructurePropanolsStereoisomerismTrimethylsilyl Compounds

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

16928081

Citation

Hernandez, Eliud, et al. "B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: Asymmetric Synthesis of Propargyl and Alpha-allenyl 3-degree-carbinols From Ketones." Organic Letters, vol. 8, no. 18, 2006, pp. 4089-91.
Hernandez E, Burgos CH, Alicea E, et al. B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones. Org Lett. 2006;8(18):4089-91.
Hernandez, E., Burgos, C. H., Alicea, E., & Soderquist, J. A. (2006). B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones. Organic Letters, 8(18), 4089-91.
Hernandez E, et al. B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: Asymmetric Synthesis of Propargyl and Alpha-allenyl 3-degree-carbinols From Ketones. Org Lett. 2006 Aug 31;8(18):4089-91. PubMed PMID: 16928081.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - B-allenyl- and B-(gamma-trimethylsilylpropargyl)-10-phenyl-9-borabicyclo[3.3.2]decanes: asymmetric synthesis of propargyl and alpha-allenyl 3-degree-carbinols from ketones. AU - Hernandez,Eliud, AU - Burgos,Carlos H, AU - Alicea,Eyleen, AU - Soderquist,John A, PY - 2006/8/25/pubmed PY - 2007/7/10/medline PY - 2006/8/25/entrez SP - 4089 EP - 91 JF - Organic letters JO - Org Lett VL - 8 IS - 18 N2 - Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(gamma-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and alpha-silylallenyl 3-degree-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic alpha-hydroxy acids and gamma-bromopropynyl carbinols, respectively. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16928081/B_allenyl__and_B__gamma_trimethylsilylpropargyl__10_phenyl_9_borabicyclo[3_3_2]decanes:_asymmetric_synthesis_of_propargyl_and_alpha_allenyl_3_degree_carbinols_from_ketones_ L2 - https://doi.org/10.1021/ol061596j DB - PRIME DP - Unbound Medicine ER -