Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries

Ma Elena Vargas-Díaz; Humberto L. Mendoza-Figueroa; M. Jonathan Fragoso-Vázquez; Francisco Ayala-Mata; Pedro Joseph-Nathan; L. Gerardo Zepeda

doi:10.1016/j.tetasy.2012.10.013

Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries

Ma Elena Vargas-Díaz, Humberto L. Mendoza-Figueroa, M. Jonathan Fragoso-Vázquez, Francisco Ayala-Mata, Pedro Joseph-Nathan, L. Gerardo Zepeda

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH₄, and NaBH₄). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH₄ ≥ NaBH₄ (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration.

Original language	English
Pages (from-to)	1588-1595
Number of pages	8
Journal	Tetrahedron Asymmetry
Volume	23
Issue number	22-23
DOIs	https://doi.org/10.1016/j.tetasy.2012.10.013
State	Published - 15 Dec 2012

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@article{bdf66c2c15e44943b037b82ba38e718d,

title = "Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries",

abstract = "New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH4 ≥ NaBH4 (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration.",

author = "Vargas-D{\'i}az, {Ma Elena} and Mendoza-Figueroa, {Humberto L.} and Fragoso-V{\'a}zquez, {M. Jonathan} and Francisco Ayala-Mata and Pedro Joseph-Nathan and Zepeda, {L. Gerardo}",

note = "Funding Information: L.G.Z. acknowledges financial support from SIP/IPN (20100702 and 20110372); L.G.Z. and M.E.V.-D. acknowledge CONACYT-Mexico (Grants 105601 and 118493, respectively); and H.L.M.-F. and F.A.-M. thank CONACYT-Mexico for fellowships. L.G.Z. and M.E.-D. are fellows of the COFAA-IPN and EDI-IPN programs.",

year = "2012",

month = dec,

day = "15",

doi = "10.1016/j.tetasy.2012.10.013",

language = "Ingl{\'e}s",

volume = "23",

pages = "1588--1595",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

number = "22-23",

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TY - JOUR

T1 - Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries

AU - Vargas-Díaz, Ma Elena

AU - Mendoza-Figueroa, Humberto L.

AU - Fragoso-Vázquez, M. Jonathan

AU - Ayala-Mata, Francisco

AU - Joseph-Nathan, Pedro

AU - Zepeda, L. Gerardo

N1 - Funding Information: L.G.Z. acknowledges financial support from SIP/IPN (20100702 and 20110372); L.G.Z. and M.E.V.-D. acknowledge CONACYT-Mexico (Grants 105601 and 118493, respectively); and H.L.M.-F. and F.A.-M. thank CONACYT-Mexico for fellowships. L.G.Z. and M.E.-D. are fellows of the COFAA-IPN and EDI-IPN programs.

PY - 2012/12/15

Y1 - 2012/12/15

N2 - New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH4 ≥ NaBH4 (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration.

AB - New (1R)-(-)-myrtenal-derived macrocycles 5a and 5b were efficiently used as chiral auxiliaries in the diastereoselective nucleophilic addition of several nucleophiles (RMgX, RLi, LiAlH4, and NaBH4). We observed that the diastereoselectivity depended on the nucleophile, with the stereoselectivity order being RMgX (>99:1 dr) > RLi (7:3 dr) > AlLiH4 ≥ NaBH4 (6:4 dr). The absolute configuration of the resulting carbinols was established by X-ray diffraction of adducts 9a and 9b, and through chemical correlation of carbinols 9b and 9c with diols of known absolute configuration.

UR - http://www.scopus.com/inward/record.url?scp=84870273156&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2012.10.013

DO - 10.1016/j.tetasy.2012.10.013

M3 - Artículo

SN - 0957-4166

VL - 23

SP - 1588

EP - 1595

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 22-23

ER -

Synthesis of acyldodecaheterocycles derived from (1R)-(-)-myrtenal and evaluation as chiral auxiliaries

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