New 2-acyl-1,3-dioxane derivatives from (1R)-(-)-myrtenal:: stereochemical effect on their relative ability as chiral auxiliaries

被引：14

作者：

Becerra-Martinez, Elvia ^{[1
]}

Velazquez-Poncea, Pedro ^{[1
]}

Sanchez-Aguilar, Miguel A. ^{[1
]}

Rodriguez-Hosteguin, Alfredo ^{[1
]}

Joseph-Nathan, Pedro ^{[2
]}

Taniariz, Joaquin ^{[1
]}

Zepeda, L. Gerardo ^{[1
]}

机构：

[1] Inst Politecn Nacl, Escuela Nacl Ciencias Biol, Dept Quim Organ, Mexico City 11340, DF, Mexico

[2] Inst Politecn Nacl, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2007年 / 18卷 / 23期

关键词：

D O I：

10.1016/j.tetasy.2007.10.047

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (IR)-(-)-myrtenal 2, were treated with (RO)(2)CHCOR3 (R-3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, >= 88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：2727 / 2737

页数：11

共 33 条

[21] First synthesis of (-)-(1R,4R)- and (+)-(1S,4S)-(7,7-dimethyl-2-methylene-bicyclo[2.2.1]hept-1-yl)-methanol:: new fenchone-derived chiral auxiliaries
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Lelièvre, M
Poissonnier, B
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[22] New lanthanide(III) complexes of chiral nonadendate macrocyclic amine derived from (1R,2R)-1,2-diaminocyclohexane and 2,6-diformyl-4-methylphenol
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JOURNAL OF ALLOYS AND COMPOUNDS, 2008, 451 (1-2) : 443 - 447
[23] Stereoselective synthesis of chiral terminal (E)-1,3-enynes derived from the aldehydes (1R)-(-)-myrtenal and (S)-(-)-perillaldehyde using the alkynyl-phosphonio complex [Ru{CCCH2(PPh3)} (η5-C9H7)(PPh3)2][PF6] as synthon
Cadierno, V
Gamasa, MP
Gimeno, J
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 621 (1-2) : 39 - 45
[24] Two chiral mononuclear and one-dimensional cadmium(II) complexes constructed by (1R,2R)-N1,N2-bis(pyridinylmethyl)cyclohexane-1,2-diamine derivatives: Effect of positional isomerism
Cheng, Lin
Cao, Qing-Na
Zhang, Li-Min
Zhang, Xiu-Ying
Gou, Shao-Hua
Fang, Lei
SOLID STATE SCIENCES, 2013, 16 : 34 - 38
[25] NEW CHIRAL POLYSILOXANES PREPARED FROM DERIVATIVES OF (+)-2-PHENYL-3-BUTENOIC OR (-)-2-PHENYL-3-BUTENOIC ACID, (R)-1-HEPTEN-3-OL AND (R)-1-CYCLOHEXYL-2-PROPEN-1-OL
AGGARWAL, SK
BRADSHAW, JS
EGUCHI, M
PARRY, S
ROSSITER, BE
MARKIDES, KE
LEE, ML
TETRAHEDRON, 1987, 43 (03) : 451 - 462
[26] X-ray crystal structure and nuclear Overhauser effect studies of cerium(IV) complexes with Schiff bases obtained from N,N′-(1R,2R)(-)-1,2-cyclohexanediamine and benzaldehyde derivatives
Szlyk, E.
Wojtczak, A.
Dobrzanska, L.
Barwiolek, M.
POLYHEDRON, 2008, 27 (02) : 765 - 776
[27] The study of Lewis acid effect on asymmetric Diels-Alder reactions of new 2-sulfinylbutadienes derived from (1R,2S,3R)-3-mercaptocamphan-2-ol
Yang, TK
Chu, HY
Lee, DS
Jian, YZ
Chou, TS
TETRAHEDRON LETTERS, 1996, 37 (26) : 4537 - 4540
[28] Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane
Cortez, Norma A.
Aguirre, Gerardo
Parra-Hake, Miguel
Somanathan, Ratnasamy
TETRAHEDRON-ASYMMETRY, 2008, 19 (11) : 1304 - 1309
[29] NEW GERMACRANE DERIVATIVES FROM NANOTHAMNUS-SERICEOUS - X-RAY MOLECULAR-STRUCTURE OF (1R,4R,5R,6R,10R)-1,10-4,5-DIEPOXY-11-HYDROXYGERMACRAN-6-YL (Z)-2-METHYLBUT-2-ENOATE
BHAT, UG
PURANIK, VG
DHANESHWAR, NN
TAVALE, SS
ROW, TNG
NAGASAMPAGI, BA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (03): : 657 - 662
[30] STRUCTURE OF 2 1,3-DIOXANE DERIVATIVES FROM 4',5'-DIMETHYLFUROCOUMARINS - 4A, 11A-DIHYDRO-4A, 11A-DIMETHYL-8H-PYRANO[3',2'-5,6]BENZOFURO[3,2-E]-1,3-DIOXAN-8-ONE AND 7A, 11A-DIHYDRO-7A, 11A-DIMETHYL-2H-PYRANO[2',3'-4,5]BENZOFURO[3,2-D] (1,3)DIOXAN-2-ONE
GUIOTTO, A
BANDOLI, G
MANZINI, P
RODIGHIERO, P
JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1987, 17 (03): : 349 - 364

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